Organization
Faculty of Environmental, Life, Natural Science and Technology Professor
Position
Professor
External link
KADOTA Isao
Degree
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博士（理学） ( 1993.3 東北大学 )
Research Interests
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Synthetic Organic Chemistry
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有機金属化合物
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天然有機化合物
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有機合成化学
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Organometalics
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Natural Product
Research Areas
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Nanotechnology/Materials / Synthetic organic chemistry
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Life Science / Bioorganic chemistry
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Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry
Education
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Tohoku University 大学院理学研究科 化学専攻
1990.4 - 1993.3
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Kochi University Graduate School of Science
1988.4 - 1990.3
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Kochi University
1984.4 - 1988.3
Research History
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岡山大学, 学術研究院環境生命自然科学学域, 教授
2023.4
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Okayama University The Graduate School of Natural Science and Technology Professor
2006.8 - 2023.3
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Tohoku University Graduate School of Science
2004.4 - 2006.7
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Tohoku University Institute of Multidisciplinary Research for Advanced Materials
2001 - 2004
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カリフォルニア大学アーバイン校 客員研究員
1999 - 2000
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東北大学反応化学研究所 講師
1996 - 2001
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Tohoku University Faculty of Science
1993 - 1996
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日本学術振興会特別研究員（東北大学）
1992 - 1993
Professional Memberships
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日本化学会
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有機合成化学協会
Committee Memberships
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岡山大学 全学交流科目部会委員（自然系交流科目班）
2025.4
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岡山大学 グローバルディスカバリープログラム運営委員
2025.4
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岡山大学 理学部副学部長（教育担当）
2025.4
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岡山大学 自然系大学院改組・学位プログラム化検討委員
2021.4 - 2023.3
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岡山大学 理学部広報委員
2021.4 - 2023.3
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岡山大学 自然生命科学研究支援センター分析計測部門SC-NMR室長
2020.4
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岡山大学 教養教育科目自然部会委員
2020.4 - 2025.3
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岡山大学グローバル人材育成院 ASEAN拠点事業統括マネージャー
2020.4 - 2025.3
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岡山大学 理学部教務委員
2020.4 - 2022.3
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岡山大学 個別試験問題作成委員
2020.4 - 2021.3
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日本化学会中国四国支部 化学教育協議会委員長
2020.3 - 2022.2
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岡山大学 グローバル人材育成院副院長（派遣・受け入れ担当）
2018.4 - 2020.3
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岡山大学 研究推進委員会委員
2018.4 - 2020.3
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日本化学会中国四国支部 化学教育協議会副委員長
2018.3 - 2020.2
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日本化学会中国四国支部 地区幹事
2016.3 - 2018.2
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文部科学省 学術調査官
2009.4 - 2011.3
Papers
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Photochemical Macrolactonization of Hydroxyaldehydes via C-H Bromination Reviewed
Sakura Kodaki, Haru Ando, Hiroyoshi Takamura, Isao Kadota, Kenta Tanaka
PRECISION CHEMISTRY 2025.11
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Recent progress on phenothiazine organophotoredox catalysis Reviewed
Tanaka, Kenta, Takamura, Hiroyoshi, Kadota, Isao
TETRAHEDRON LETTERS 169 155745 2025.10
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Nitrogen distribution and nitrogen isotope fractionation in synthetic 2:1 phyllosilicates under hydrothermal conditions at 200 °C and saturated vapor pressure Reviewed
Jaeguk Jo, Toshiro Yamanaka, Youko Miyoshi, Masaya Suzuki, Yoshihiro Kuwahara, Isao Kadota, Hitoshi Chiba, Bum Han Lee
APPLIED GEOCHEMISTRY 187 2025.8
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Mizutani, Asuka, Kondo, Momo, Itakura, Shoko, Takamura, Hiroyoshi, Hoshino, Yujiro, Nishikawa, Makiya, Kadota, Isao, Kusamori, Kosuke, Tanaka, Kenta
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 98 ( 6 ) uoaf044 2025.5
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Strongly Oxidizing Thiapyrylium Salt for Organophotoredox Catalysis Reviewed
Mohamed R. El-kholany, Takeru Senoo, Asuka Mizutani, Hiroyoshi Takamura, Takayoshi Suzuki, Isao Kadota, Kenta Tanaka
ORGANIC LETTERS 27 ( 19 ) 4870 - 4874 2025.5
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Antifouling Activity of Xylemin, Its Structural Analogs, and Related Polyamines Reviewed
Takamura, Hiroyoshi, Yorisue, Takefumi, Tanaka, Kenta, Kadota, Isao
CHEMISTRY & BIODIVERSITY 22 ( 4 ) e202403213 2025.2
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Miyamoto, Atsuya, Takamura, Hiroyoshi, Kadota, Isao, Tanaka, Kenta
CHEMICAL COMMUNICATIONS 61 ( 89 ) 17364 - 17367 2025
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Horiuchi, Shuta, Oishi, Masato, Mizutani, Asuka, Takamura, Hiroyoshi, Kadota, Isao, Tanaka, Kenta
CHEMICAL COMMUNICATIONS 61 ( 84 ) 2025
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Synthesis of Ozonides Mediated by Molecular Sieve Under Solvent-Free Conditions Reviewed International journal
Mohamed R. El-kholany, Nana Kishimoto, Kenta Tanaka, Hiroyoshi Takamura, Isao Kadota
Tetrahedron 134137 - 134137 2024.7
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Strongly reducing helical phenothiazines as recyclable organophotoredox catalysts Reviewed International journal
Haru Ando, Hiroyoshi Takamura, Isao Kadota, Kenta Tanaka
Chemical Communications 60 ( 36 ) 4765 - 4768 2024
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Total synthesis and structure–antifouling activity relationship of scabrolide F Reviewed International journal
Hiroyoshi Takamura, Yuki Sugitani, Ryohei Morishita, Takefumi Yorisue, Isao Kadota
Organic & Biomolecular Chemistry 22 ( 28 ) 5739 - 5747 2024
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A direct oxidative esterification of aldehydes with alcohols mediated by photochemical C–H bromination Reviewed International journal
Haru Ando, Sakura Kodaki, Hiroyoshi Takamura, Isao Kadota, Kenta Tanaka
Organic & Biomolecular Chemistry 22 ( 46 ) 2024
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Efficient Method for the Preparation of Ozonides Under Dry Conditions Reviewed International coauthorship International journal
Mohamed R. El-kholany, Nana Kishimoto, Kenta Tanaka, Hiroyoshi Takamura, Isao Kadota
Bulletin of the Chemical Society of Japan 96 ( 12 ) 1316 - 1318 2023.12
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Chemical synthesis and antifouling activity of monoterpene–furan hybrid molecules Reviewed International journal
Hiroyoshi Takamura, Yuya Kinoshita, Takefumi Yorisue, Isao Kadota
Organic and Biomolecular Chemistry 21 ( 3 ) 632 - 638 2023
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Relative stereochemical determination of the C61–C83 fragment of symbiodinolide using a stereodivergent synthetic approach Reviewed International journal
Hiroyoshi Takamura, Kosuke Hattori, Takumi Ohashi, Taichi Otsu, Isao Kadota
Organic and Biomolecular Chemistry 21 ( 44 ) 8837 - 8848 2023
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Total Synthesis of Scabrolide F Reviewed International journal
Hiroyoshi Takamura, Yuki Sugitani, Ryohei Morishita, Isao Kadota
Organic Letters 24 ( 42 ) 7845 - 7849 2022.10
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新しい生活
門田 功
化学と教育 68 ( 11 ) 459 - 459 2020.11
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Chemical Synthesis and Biological Effect on Xylem Formation of Xylemin and Its Analogues Reviewed International journal
Hiroyoshi Takamura, Hiroyasu Motose, Taichi Otsu, Shiori Shinohara, Ryugo Kouno, Isao Kadota, Taku Takahashi
European Journal of Organic Chemistry 2020 ( 18 ) 2745 - 2753 2020.5
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Hiroyoshi Takamura, Isao Kadota
Journal of Synthetic Organic Chemistry, Japan 77 ( 12 ) 1190 - 1200 2019.12
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ブテノライドを構造基盤とする付着阻害活性分子の合成と評価
高村浩由, 菊地崇浩, 大津泰知, 大橋拓実, 門田功, 遠藤紀之, 福田祐司
Sessile Organisms 36 ( 2 ) 2019
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Late-stage divergent synthesis and antifouling activity of geraniol-butenolide hybrid molecules Reviewed
Hiroyoshi Takamura, Takumi Ohashi, Takahiro Kikuchi, Noriyuki Endo, Yuji Fukuda, Isao Kadota
Organic and Biomolecular Chemistry 15 ( 26 ) 5549 - 5555 2017
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Hiroyoshi Takamura, Takahiro Kikuchi, Noriyuki Endo, Yuji Fukuda, Isao Kadota
Organic Letters 18 ( 9 ) 2110 - 2113 2016.5
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Chemical control of xylem differentiation by thermospermine, xylemin, and auxin Reviewed
Yoshimoto Kaori, Takamura Hiroyoshi, Kadota Isao, Motose Hiroyasu, Takahashi Taku
Scientific Reports 6 ( 6 ) 21487 - 21487 2016.2
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Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide Reviewed
Hiroyoshi Takamura, Takayuki Fujiwara, Yohei Kawakubo, Isao Kadota, Daisuke Uemura
Chemistry - A European Journal 22 ( 6 ) 1979 - 1983 2016.2
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Hiroyoshi Takamura, Takayuki Fujiwara, Yohei Kawakubo, Isao Kadota, Daisuke Uemura
Chemistry - A European Journal 22 ( 6 ) 2183 - 2183 2016.2
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Stereodivergent Synthesis and Stereochemical Reassignment of the C79-C104 Fragment of Symbiodinolide Reviewed
Hiroyoshi Takamura, Takayuki Fujiwara, Yohei Kawakubo, Isao Kadota, Daisuke Uemura
Chemistry - A European Journal 22 ( 6 ) 1984 - 1996 2016.2
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Convergent synthesis of the EFGH ring system of ciguatoxin CTX3C Reviewed
Isao Kadota, Yuki Sato, Naoya Fujita, Hiroyoshi Takamura, Yoshinori Yamamoto
TETRAHEDRON 71 ( 37 ) 6547 - 6558 2015.9
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Stereodivergent Synthesis and Relative Stereostructure of the C1–C13 Fragment of Symbiodinolide Reviewed
Hiroyoshi Takamura, Hiroko Wada, Mao Ogino, Takahiro Kikuchi, Isao Kadota, Daisuke Uemura
The Journal of Organic Chemistry 80 ( 6 ) 3111 - 3123 2015.3
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STEREOCONTROLLED SYNTHESIS OF THE C1-C7 FRAGMENT OF ENIGMAZOLE A Reviewed
Takayuki Kishi, Yuka Fujisawa, Hiroyoshi Takamura, Isao Kadota
HETEROCYCLES 89 ( 2 ) 515 - 522 2014.2
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IMPROVDED SYNTHESIS OF THE A-E RING SEGMENT OF CIGUATOXIN CTX3C Reviewed
Kengo Shiroma, Hiroki Asakura, Tokihiro Tanaka, Hiroyoshi Takamura, Isao Kadota
HETEROCYCLES 88 ( 2 ) 969 - 973 2014.1
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Stereoselective synthesis of the C79-C97 fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Takayuki Fujiwara, Isao Kadota, Daisuke Uemura
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 9 1931 - 1935 2013.9
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Takamura Hiroyoshi, Wada Hiroko, Lu Nan, Ohno Osamu, Suenaga Kiyotake, Kadota Isao
Journal of Organic Chemistry 78 ( 6 ) 2443 - 2454 2013.3
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Hiroyoshi Takamura, Kohei Iwamoto, Eiji Nakao, Isao Kadota
ORGANIC LETTERS 15 ( 5 ) 1108 - 1111 2013.3
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Kengo Shiroma, Hiroyoshi Takamura, Isao Kadota
HETEROCYCLES 86 ( 2 ) 997 - 1001 2012.12
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Stereoselective synthesis of the C94-C104 fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Kosuke Tsuda, Yohei Kawakubo, Isao Kadota, Daisuke Uemura
Tetrahedron Letters 53 ( 33 ) 4317 - 4319 2012.8
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A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C Reviewed
Hiroyoshi Takamura, Takashi Abe, Naoki Nishiuma, Rie Fujiwara, Takahiko Tsukeshiba, Isao Kadota
TETRAHEDRON 68 ( 10 ) 2245 - 2260 2012.3
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Convergent Synthesis of the HIJKLM Ring System of Ciguatoxin CTX3C Reviewed
Hiroyoshi Takamura, Naoki Nishiuma, Takashi Abe, Isao Kadota
ORGANIC LETTERS 13 ( 17 ) 4704 - 4707 2011.9
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Total synthesis and absolute configuration of (-)-gummiferol Reviewed
Hiroyoshi Takamura, Hiroko Wada, Nan Lu, Isao Kadota
Organic Letters 13 ( 14 ) 3644 - 3647 2011.7
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Hiroyoshi Takamura, Yuichiro Kadonaga, Isao Kadota, Daisuke Uemura
Tetrahedron 66 ( 38 ) 7569 - 7576 2010.9
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A new method for the stereoselective construction of angular methyl group of fuzed cyclic ethers Reviewed
Isao Kadota, Takayuki Kishi, Yuka Fujisawa, Yuji Yamagami, Hiroyoshi Takamura
TETRAHEDRON LETTERS 51 ( 30 ) 3960 - 3961 2010.7
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Total synthesis of brevenal Reviewed
Hiroyoshi Takamura, Yuji Yamagami, Takayuki Kishi, Shigetoshi Kikuchi, Yuichi Nakamura, Isao Kadota, Yoshinori Yamamoto
TETRAHEDRON 66 ( 29 ) 5329 - 5344 2010.7
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Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Yuichiro Kadonaga, Isao Kadota, Daisuke Uemura
TETRAHEDRON LETTERS 51 ( 19 ) 2603 - 2605 2010.5
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Total Synthesis of Brevenal
Yamagami Yuji, Kikuchi Shigetoshi, Nakamura Yuichi, Kishi Takayuki, Takamura Hiroyoshi, Kadota Isao, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 51 ) 223 - 228 2009.9
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Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Yuichiro Kadonaga, Yoshi Yamano, Chunguang Han, Isao Kadota, Daisuke Uemura
TETRAHEDRON 65 ( 36 ) 7449 - 7456 2009.9
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Hiroyoshi Takamura, Takeshi Murata, Takahiro Asai, Isao Kadota, Daisuke Uemura
JOURNAL OF ORGANIC CHEMISTRY 74 ( 17 ) 6658 - 6666 2009.9
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Convergent synthesis of the A-E ring segment of ciguatoxin CTX3C Reviewed
Isao Kadota, Takashi Abe, Miyuki Uni, Hiroyoshi Takamura, Yoshinori Yamamoto
TETRAHEDRON 65 ( 37 ) 7784 - 7789 2009.9
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Selective cleavage of primary MPM ethers with TMSI/Et3N Reviewed
Isao Kadota, Yuji Yamagami, Naoya Fujita, Hiroyoshi Takamura
TETRAHEDRON LETTERS 50 ( 31 ) 4552 - 4553 2009.8
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Synthesis and structural revision of symbiodinolide C23-C34 fragment Reviewed
Takeshi Murata, Masayuki Sano, Hiroyoshi Takamura, Isao Kadota, Daisuke Uemura
Journal of Organic Chemistry 74 ( 13 ) 4797 - 4803 2009.7
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Total Synthesis of Brevenal Reviewed
Hiroyoshi Takamura, Shigetoshi Kikuchi, Yuichi Nakamura, Yuji Yamagami, Takayuki Kishi, Isao Kadota, Yoshinori Yamamoto
ORGANIC LETTERS 11 ( 12 ) 2531 - 2534 2009.6
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Synthesis and structural determination of the C33-C42 fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Yuichiro Kadonaga, Yoshi Yamano, Chunguang Han, Yoko Aoyama, Isao Kadota, Daisuke Uemura
Tetrahedron Letters 50 ( 8 ) 863 - 866 2009.2
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A TRANSANNULAR DIELS-ALDER STRATEGY TO THE CONSTRUCTION OF THE CDE RING SYSTEM OF NAKITERPIOSIN Reviewed
Hiroyoshi Takamura, Yuji Yamagami, Tomonori Ito, Masahiro Ito, Hirokazu Arimoto, Isao Kadota, Daisuke Uemura
HETEROCYCLES 77 ( 1 ) 351 - 364 2009.1
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Stereocontrolled synthesis of the C79-C96 fragment of symbiodinolide Reviewed
Hiroyoshi Takamura, Junki Ando, Takashi Abe, Takeshi Murata, Isao Kadota, Daisuke Uemura
TETRAHEDRON LETTERS 49 ( 31 ) 4626 - 4629 2008.7
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A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin Reviewed
Isao Kadota, Takashi Abe, Miyuki Uni, Hiroyoshi Takamura, Yoshinori Yamamoto
TETRAHEDRON LETTERS 49 ( 22 ) 3643 - 3647 2008.5
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Solvent-controlled stereoselective formation of a cyclic ether in the lewis acid-mediated allylation of an alpha-Chloroacetoxy acyclic ether. Very high stereoselectivity in CH3CN vs low stereoselectivity in CH2Cl2 Reviewed
Ilya D. Gridnev, Shigetoshi Kikuchi, Abeda S. Touchy, Isao Kadota, Yoshinori Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 72 ( 22 ) 8371 - 8375 2007.10
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A convergent approach to the formal total synthesis of hemibrevetoxin B Reviewed
Isao Kadota, Takashi Abe, Yukako Ishitsuka, Abeda S. Touchy, Ryoko Nagata, Yoshinori Yamamoto
TETRAHEDRON LETTERS 48 ( 2 ) 219 - 221 2007.1
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Isao Kadota, Takashi Abe, Yukako Ishitsuka, Abeda S. Touch, Ryoko Nagata, Yoshinori Yamamoto
HETEROCYCLES 74 ( - ) 617 - 627 2007
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Stereocontrolled synthesis of the IJK ring segment of yessotoxin Reviewed
Isao Kadota, Takashi Abe, Yuki Sato, Chizuko Kabuto, Yoshinori Yamamoto
TETRAHEDRON LETTERS 47 ( 37 ) 6545 - 6548 2006.9
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P-141 Convergent Synthesis of Hemibrevetoxin B
Ishitsuka Yukako, Abeda Touchy, Nagata Ryoko, Kadota Isao, Yamamoto Yoshinori
International Symposium on the Chemistry of Natural Products 2006 "P - 141" 2006.7
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P-140 Synthesis of the IJK Ring Segment of Yessotoxin
Abe Takashi, Sato Yuki, Kadota Isao, Yamamoto Yoshinori
International Symposium on the Chemistry of Natural Products 2006 "P - 140" 2006.7
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Improved synthesis of the A-G ring segment of brevetoxin B Reviewed
Isao Kadota, Hiroki Nishii, Hiroki Ishioka, Hiroyoshi Takamura, Yoshinori Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 71 ( 11 ) 4183 - 4187 2006.5
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Convergent synthesis of the FGHI ring segment of yessotoxin Reviewed
Isao Kadota, Hirokazu Ueno, Yuki Sato, Yoshinori Yamamoto
Tetrahedron Letters 47 ( 1 ) 89 - 92 2006.1
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P-31 Total Synthesis of Brevetoxin B
Takamura Hiroyoshi, Nishii Hiroki, Ishioka Hiroki, Kadota Isao, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 47 ) 325 - 330 2005.9
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Total synthesis of brevetoxin B Reviewed
Kadota, I, H Takamura, H Nishii, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 127 ( 25 ) 9246 - 9250 2005.6
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NT Patil, HY Wu, Kadota, I, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 69 ( 25 ) 8745 - 8750 2004.12
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37(D-7) Synthetic Study of Brevetoxin B
Takamura Hiroyoshi, Nishii Hiroki, Kadota Isao, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 46 ) 197 - 202 2004.10
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26 Syntheic Study of Gambierol
Takamura Hiroyoshi, Ohno Akio, Sato Kumi, Matsuda Kumiko, Yamamoto Yoshinori, Kadota Isao
Symposium on the Chemistry of Natural Products, symposium papers ( 44 ) 151 - 156 2002.9
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41 Convergent Synthesis of Polycyclic Ethers and Its Application to the Total Synthesis of Gambierol
Kadota Isao, Ohno Akio, Takamura Hiroyoshi, Sato Kumi, Matsuda Kumiko, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 43 ) 241 - 246 2001.9
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38 Synthetic Study of Gambierol
Kadota Isao, Kadowaki Chie, Park Choul-Hong, Ohno Akio, Ohtaka Manabu, Oguro Nao, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 40 ) 223 - 228 1998.8
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119(P62) STEREOSELECTIVE SYNTHESIS OF POLYCYCLIC ETHERS AND RELATED HETEROCYCLES
Kadota Isao, Park Jung-Youl, Saya Shioko, Kawada Miho, Yamamoto Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 38 ) 709 - 714 1996.9
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Total synthesis of hemibrevetoxin B via the allylic tin methodology Reviewed
Isao Kadota, Yoshinori Yamamoto
Main Group Metal Chemistry 19 ( 6 ) 361 - 366 1996
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24 TOTAL SYNTHESIS OF HEMIBREVETOXIN B
KADOTA Isao, YAMAMOTO Yoshinori
Symposium on the Chemistry of Natural Products, symposium papers ( 37 ) 139 - 143 1995.9
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11 Development of a Novel Cyclization Reaction via Group 14 Organometallics and its Application to the Synthesis of Polyether Natural Products
Kadota I., Gevorgan V., Yamada J., Yamamoto Y.
Symposium on the Chemistry of Natural Products, symposium papers ( 33 ) 78 - 85 1991.9
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64(P1-12) SYNTHESES OF OPTICALLY ACTIVE NATURAL PRODUCTS VIA C-C BOND FORMATION OF TRIFLATES
Kotsuki H., Kadota I., Ochi M.
Symposium on the Chemistry of Natural Products, symposium papers ( 31 ) 490 - 497 1989.9
MISC
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Stereocontrolled synthesis of the macrolactone core of neopeltolide Reviewed
Andreas Meissner, Nobuhiro Tanaka, Hiroyoshi Takamura, Isao Kadota
Tetrahedron Letters 60 ( 5 ) 432 - 434 2019.1
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Formal total synthesis of enigmazole A Reviewed
Andreas Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Hiroyoshi Takamura, Isao Kadota
Tetrahedron Letters 59 ( 51 ) 4492 - 4495 2018.12
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Hiroyoshi Takamura, Takahiro Kikuchi, Kohei Iwamoto, Eiji Nakao, Naoki Harada, Taichi Otsu, Noriyuki Endo, Yuji Fukuda, Osamu Ohno, Kiyotake Suenaga, Yue-Wei Guo, Isao Kadota
The Journal of Organic Chemistry 83 ( 18 ) 11028 - 11056 2018.9
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97 ( 2 ) 1157 - 1164 2018.9
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Jo Jaeguk, Yamanaka Toshiro, Kashimura Tomoki, Okunishi Yusuke, Kuwahara Yoshihiro, Kadota Isao, Miyoshi Youko, Ishibashi Jun-ichiro, Chiba Hitoshi
GEOCHEMICAL JOURNAL 52 ( 4 ) 317 - 333 2018.7
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Improved Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C by Using Intramolecular Allylations Reviewed
Tokihiro Tanaka, Hiroki Asakura, Rie Fujiwara, Kentaro Kumamoto, Hiroaki Izuka, Kengo Shiroma, Hiroyoshi Takamura, Isao Kadota
Bulletin of the Chemical Society of Japan 91 ( 4 ) 507 - 514 2018.4
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Convergent total synthesis of (−)-dactylolide Reviewed
Tokihiro Tanaka, Yuto Murai, Takayuki Kishi, Hiroyoshi Takamura, Isao Kadota
Tetrahedron Letters 59 ( 8 ) 763 - 766 2018.2
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ゲラニオール-ブテノライドハイブリッド分子の発散的合成と付着阻害活性
大橋拓実, 菊地崇浩, 遠藤紀之, 福田祐司, 高村浩由, 門田功
日本化学会春季年会講演予稿集(CD-ROM) 98th 2018
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Total Synthesis of Rhoiptelol B Reviewed
Isao Kadota, Nobuhiro Tanaka, Hiroyoshi Takamura
HETEROCYCLES 97 ( 2 ) 1157 - 1157 2018
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Hiroyoshi Takamura, Tomoya Katsube, Kazuki Okamoto, Isao Kadota
Chemistry - A European Journal 23 ( 68 ) 17191 - 17194 2017.12
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サルコフィトノライド類の統一的合成と構造活性相関に関する研究
高村浩由, 菊地崇浩, 岩本浩平, 仲尾英史, 原田直樹, 大野修, 末永聖武, 遠藤紀之, 福田祐司, 門田功
天然有機化合物討論会講演要旨集(Web) 57th 2015
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Synthetic Study of the Polyol Natural Product Symbiodinolide toward the Structural Elucidation
72 ( 1 ) 6 - 17 2014.1
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造解明を指向したポリオール天然物シンビオジノライドの合成研究 Reviewed
髙村 浩由, 門田 功
有機合成化学協会誌 72 2 - 13 2014
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Synthetic Study of Marine Natural Products Having Potent Biological Activities
1 - 4 2013
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Total synthesis of brevetoxin B
Isao Kadota, Hiroyoshi Takamura
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 65 ( 5 ) 430 - 438 2007.5
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Kadota, I, Y Yamamoto
ACCOUNTS OF CHEMICAL RESEARCH 38 ( 5 ) 423 - 432 2005.5
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A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols
Kadota, I, YQ Hu, GK Packard, SD Rychnovsky
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA 101 ( 33 ) 11992 - 11995 2004.8
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A new approach to the synthesis of cyclic ethers via the intermolecular allylation of alpha-acetoxy ethers and ring-closing metathesis
Kadota, I, H Uyehara, Y Yamamoto
TETRAHEDRON 60 ( 34 ) 7361 - 7365 2004.8
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A new approach to the synthesis of cyclic ethers via the intermolecular allylation of alpha-acetoxy ethers and ring-closing metathesis
Kadota, I, H Uyehara, Y Yamamoto
TETRAHEDRON 60 ( 34 ) 7361 - 7365 2004.8
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Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst
NT Patil, Kadota, I, A Shibuya, YS Gyoung, Y Yamamoto
ADVANCED SYNTHESIS & CATALYSIS 346 ( 7 ) 800 - 804 2004.6
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Palladium-catalyzed intramolecular asymmetric hydroamination of alkynes
LM Lutete, Kadota, I, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 126 ( 6 ) 1622 - 1623 2004.2
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Convergent synthesis of the A-F ring segment of yessotoxin and adriatoxin
Isao Kadota, Hirokazu Ueno, Yoshinori Yamamoto
Tetrahedron Letters 44 ( 50 ) 8935 - 8938 2003.12
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Convergent synthesis of the A-F ring segment of yessotoxin and adriatoxin
Kadota, I, H Ueno, Y Yamamoto
TETRAHEDRON LETTERS 44 ( 50 ) 8935 - 8938 2003.12
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A simple and practical method for the stereoselective synthesis of (Z)-1-iodo-1-alkenes from 1,1-diiodo-1-alkenes
Kadota, I, H Ueno, A Ohno, Y Yamamoto
TETRAHEDRON LETTERS 44 ( 48 ) 8645 - 8647 2003.11
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Convergent synthesis of the F-K ring segment of brevetoxin B
Isao Kadota, Naoko Nishina, Hiroki Nishii, Shigetoshi Kikuchi, Yoshinori Yamamoto
Tetrahedron Letters 44 ( 43 ) 7929 - 7932 2003.10
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Convergent synthesis of the F-K ring segment of brevetoxin B
Kadota, I, N Nishina, H Nishii, S Kikuchi, Y Yamamoto
TETRAHEDRON LETTERS 44 ( 43 ) 7929 - 7932 2003.10
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Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities
Kadota, I, H Takamura, K Sato, A Ohno, K Matsuda, M Satake, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 125 ( 39 ) 11893 - 11899 2003.10
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Kadota, I, H Takamura, K Sato, A Ohno, K Matsuda, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 125 ( 1 ) 46 - 47 2003.1
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Hydroamination of alkynes catalyzed by palladium/benzoic acid
LM Lutete, Kadota, I, A Shibuya, Y Yamamoto
HETEROCYCLES 58 ( - ) 347 - 357 2002.11
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Kadota, I, H Takamura, K Sato, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 67 ( 10 ) 3494 - 3498 2002.5
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Kadota, I, A Ohno, K Matsuda, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124 ( 14 ) 3562 - 3566 2002.4
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Syntheses of the AB and EFGH ring segments of gambierol
Kadota, I, C Kadowaki, CH Park, H Takamura, K Sato, PWH Chan, S Thorand, Y Yamamoto
TETRAHEDRON 58 ( 10 ) 1799 - 1816 2002.3
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Synthetic studies towards gambierol. Part 1: Synthesis of the AB ring segment
Isao Kadota, Choul-Hong Park, Kumi Sato, Yoshinori Yamamoto
Tetrahedron Letters 42 ( 35 ) 6195 - 6197 2001.8
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Synthetic studies towards gambierol. Part 1: Synthesis of the AB ring segment
Kadota, I, CH Park, K Sato, Y Yamamoto
TETRAHEDRON LETTERS 42 ( 35 ) 6195 - 6197 2001.8
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Synthetic studies towards gambierol. Part 2: Synthesis of the EFGH ring segment
Kadota, I, C Kadowaki, H Takamura, Y Yamamoto
TETRAHEDRON LETTERS 42 ( 35 ) 6199 - 6202 2001.8
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Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes
Kadota, I, LM Lutete, A Shibuya, Y Yamamoto
TETRAHEDRON LETTERS 42 ( 35 ) 6207 - 6210 2001.8
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Kadota, I, A Ohno, K Matsuda, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 123 ( 27 ) 6702 - 6703 2001.7
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Concise synthesis of cyclic ethers via the palladium-catalyzed coupling of ketene acetal triflates and a zinc homoenolate. Synthesis of the DE and GH ring segments of gambierol
Kadota, I, H Takamura, K Sato, Y Yamamoto
TETRAHEDRON LETTERS 42 ( 28 ) 4729 - 4731 2001.7
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Synthesis of the A ring segment of gambieric acid
Isao Kadota, Nao Oguro, Yoshinori Yamamoto
Tetrahedron Letters 42 ( 21 ) 3645 - 3647 2001.5
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Synthesis of the J ring segment of gambieric acid
Isao Kadota, Hiroyoshi Takamura, Yoshinori Yamamoto
Tetrahedron Letters 42 ( 21 ) 3649 - 3651 2001.5
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Synthesis of the J ring segment of gambieric acid
Kadota, I, H Takamura, Y Yamamoto
TETRAHEDRON LETTERS 42 ( 21 ) 3649 - 3651 2001.5
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Synthesis of the A Ring of Gambieric Acid
KADOTA I, OGURO N, YAMAMOTO Y
Tetrahedron Lett. 42 ( 21 ) 3645 - 3647 2001
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A novel convergent approach to trans-fused polyether frameworks based on the reaction of vinylstannanes and triflates and its application to a synthetic study of the EFGH ring system of gambierol
C Kadowaki, PWH Chan, Kadota, I, Y Yamamoto
TETRAHEDRON LETTERS 41 ( 30 ) 5769 - 5772 2000.7
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Diastereo- and enantioselective synthesis of beta-amino cyclic ethers via the intramolecular reaction of gamma-alkoxyallylstannane with imine
JY Park, Kadota, I, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 64 ( 13 ) 4901 - 4908 1999.6
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Palladium benzoic acid catalyzed hydroamination of alkynes
Kadota, I, A Shibuya, LM Lutete, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 64 ( 13 ) 4570 - 4571 1999.6
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Palladium acetic acid catalyzed allylation of some pronucleophiles with simple alkynes
Kadota, I, A Shibuya, YS Gyoung, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 120 ( 39 ) 10262 - 10263 1998.10
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Stereocontrolled total synthesis of hemibrevetoxin B
Kadota, I, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 63 ( 19 ) 6597 - 6606 1998.9
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Synthesis of the E ring of gambierol
Kadota, I, C Kadowaki, N Yoshida, Y Yamamoto
TETRAHEDRON LETTERS 39 ( 35 ) 6369 - 6372 1998.8
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Synthesis of the AB ring system of gambierol
Kadota, I, CH Park, M Ohtaka, N Oguro, Y Yamamoto
TETRAHEDRON LETTERS 39 ( 35 ) 6365 - 6368 1998.8
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Synthesis of the H ring of gambierol
Kadota, I, A Ohno, Y Matsukawa, Y Yamamoto
TETRAHEDRON LETTERS 39 ( 35 ) 6373 - 6376 1998.8
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全合成 (特集 21世紀の化学--残された大テ-マ 逆説"The End of Chemistry")
山本 嘉則, 門田 功
化学 53 ( 5 ) 14 - 16 1998.5
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Asymmetric synthesis of beta-amino cyclic ethers via the intramolecular reaction of gamma-alkoxyallylstannane with chiral imine
JY Park, CH Park, Kadota, I, Y Yamamoto
TETRAHEDRON LETTERS 39 ( 13 ) 1791 - 1794 1998.3
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21世紀の化学"全合成"
化学 53 ( 5 ) 14 1998
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Chemistry in 21st Century "Total Synthesis"
Chemistry 53 ( 5 ) 14 1998
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Novel route to the synthesis of hydroxylated pyrrolidine derivatives via the intramolecular reaction of gamma-aminoallystannane with aldehyde. Total synthesis of (+)-preussin
Kadota, I, S Saya, Y Yamamoto
HETEROCYCLES 46 ( 1 ) 335 - 348 1997.12
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Asymmetric total syntheses of hydroxylated piperidine alkaloids via the intramolecular reaction of gamma-aminoallylstannane with aldehyde
Kadota, I, M Kawada, Y Muramatsu, Y Yamamoto
TETRAHEDRON-ASYMMETRY 8 ( 23 ) 3887 - 3893 1997.12
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Total synthesis of (+)-desoxoprosopinine via the intramolecular reaction of γ-aminoallylstannane
Isao Kadota, Miho Kawada, Yoko Muramatsu, Yoshinori Yamamoto
Tetrahedron Letters 38 ( 42 ) 7469 - 7470 1997.10
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Kadota, I, M Kawada, Gevorgyan, V, Y Yamamoto
JOURNAL OF ORGANIC CHEMISTRY 62 ( 21 ) 7439 - 7446 1997.10
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Total synthesis of (+)-desoxoprosopinine via the intramolecular reaction of gamma-aminoallylstannane
Kadota, I, M Kawada, Y Muramatsu, Y Yamamoto
TETRAHEDRON LETTERS 38 ( 42 ) 7469 - 7470 1997.10
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Kadota, I, Y Yamamoto
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 55 ( 7 ) 619 - 630 1997.7
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Palladium catalyzed addition of carbon pronucleophiles to conjugated enynes
Gevorgyan, V, C Kadowaki, MM Salter, Kadota, I, S Saito, Y Yamamoto
TETRAHEDRON 53 ( 27 ) 9097 - 9106 1997.7
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Regioselective synthesis of 1,3,5-unsymmetrically substituted benzenes via the palladium-catalyzed cyclotrimerization of 1,3-diynes
A Takeda, A Ohno, Kadota, I, Gevorgyan, V, Y Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 119 ( 19 ) 4547 - 4548 1997.5
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Novel Route to the Synthesis of Hydroxylated Pyrrolidine Perivatives via the Intramolecular Reaction of gamma-Aminoallylstannane with Aldehycle. Total Synthesis of (+)-Preussin
Heterocycles 46 335 - 348 1997
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Organometallic-Lewis Acid Complex System
YAMAMOTO Yoshinori, KADOTA Isao
50 ( 10 ) 1486 - 1488 1997
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アリルスズの分子内反応を用いるポリ環状エーテルおよび関連ヘテロ環化合物の立体選択的合成
門田 功, 山本 嘉則
有機合成化学協会誌 55 ( 7 ) 619 - 630 1997
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Organometallics-Lewis Acid Complex System
Chemistry and Chemical Industry 50 1486 - 1488 1997
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Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde
Isao Kadota, Daigo Hatakeyama, Katsura Seki, Yoshinori Yamamoto
Tetrahedron Letters 37 ( 17 ) 3059 - 3062 1996.4
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A general and efficient method for the preparation of gamma-alkoxyallylstannanes via an acetal cleavage
Kadota, I, T Sakaihara, Y Yamamoto
TETRAHEDRON LETTERS 37 ( 18 ) 3195 - 3198 1996.4
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Intramolecular reaction of gamma-alkoxyallylstannane with hydrazone: Stereoselective synthesis of beta-aminotetrahydro-pyran and -furan
Kadota, I, JY Park, Y Yamamoto
CHEMICAL COMMUNICATIONS ,841-842 ( 7 ) 841 - 842 1996.4
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Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde
Kadota, I, D Hatakeyama, K Seki, Y Yamamoto
TETRAHEDRON LETTERS 37 ( 17 ) 3059 - 3062 1996.4
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Novel route to the synthesis of hydroxylated piperidine and pyrrolidine derivatives via the intramolecular reaction of gamma-aminoallylstannane with aldehyde
Kadota, I, M Kawada, S Saya, Y Yamamoto
TETRAHEDRON LETTERS 37 ( 12 ) 2109 - 2112 1996.3
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Total Synthesis of Hemibrevetoxin B via the Allylic Tin Method
Main Group Metal Chemistry 19 361 - 366 1996
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Total synthesis of hemibrevetoxin B via the allylic tin methodology
Kadota, I, Y Yamamoto
MAIN GROUP METAL CHEMISTRY 19 ( 6 ) 361 - 366 1996
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TOTAL SYNTHESIS OF HEMIBREVETOXIN-B
KADOTA, I, P JUNGYOUL, N KOUMURA, G POLLAUD, Y MATSUKAWA, Y YAMAMOTO
TETRAHEDRON LETTERS 36 ( 32 ) 5777 - 5780 1995.8
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NICKEL-CATALYZED IMINE ALDOL REACTIONS BETWEEN ACTIVATED IMINES AND PRONUCLEOPHILES
N SHIDA, Y KUBOTA, H FUKUI, N ASAO, KADOTA, I, Y YAMAMOTO
TETRAHEDRON LETTERS 36 ( 28 ) 5023 - 5026 1995.7
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ASYMMETRIC DIELS-ALDER REACTIONS OF TMHD-ACRYLATE USING TICL4-CENTER-DOT(ARNHG)(M) COMPLEXED LEWIS-ACIDS
KADOTA, I, K KOBAYASHI, N ASAO, Y YAMAMOTO
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS ,1271-1272 ( 12 ) 1271 - 1272 1995.6
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Asymmetric Diels-Alder Reaction of TMHD-acrylate using TiCl4(ArnHg)m Complex Lewis Acids
Journal of Chemical Society, Chemical Communication ,1271-1272 1995
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Tri-butylchlorostannane
Encyclopedia of Reagents for Organic Synthesis 1995
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Tri-butylchlorostannane
Encyclopedia of Reagents for Organic Synthesis 1995
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CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANE - A NEW CHIRAL REAGENT FOR THE ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS
KADOTA, I, K KOBAYASHI, H OKANO, N ASAO, Y YAMAMOTO
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE 132 ( 5-6 ) 615 - 623 1995
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HIGHLY STEREOCONTROLLED FORMAL TOTAL SYNTHESIS OF HEMIBREVETOXIN-B
Y YAMAMOTO, KADOTA, I
BULLETIN DES SOCIETES CHIMIQUES BELGES 103 ( 9-10 ) 619 - 628 1994.9
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KADOTA, I, K MIURA, Y YAMAMOTO
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS ,1953-1954 ( 17 ) 1953 - 1954 1994.9
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Stereocontrolled Synthesis of the 6-7-7-6 Ring System of Polycyclic Ethers via the Intramolecular Reaction with omega-Tributyl stannyl Ether Aldehydes
Main Group Metal Chemistry 17 269 - 289 1994
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Stereocontrolled Synthesis of the 6-7-7-6 Ring System of Polycyclic Ethers via the Intramolecular Reaction with omega-Tributyl stannyl Ether Aldehydes
Main Group Metal Chemistry 17 269 - 289 1994
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Highly Stereocontrolled Formal Total Synthesis of Hemibrevetoxin B
Bulletin des Societies Chimiques Belges 103 619 - 629 1994
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STEREOCONTROLLED SYNTHESIS OF THE HEMIBREVETOXIN RING-SYSTEM VIA AN ALLYLIC TIN METHOD
KADOTA, I, Y MATSUKAWA, Y YAMAMOTO
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS ,1638-1641 ( 21 ) 1638 - 1641 1993.11
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Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation
Vladimir Gevorgyan, Isao Kadota, Yoshinori Yamamoto
Tetrahedron Letters 34 ( 8 ) 1313 - 1316 1993.2
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CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION
GEVORGYAN, V, KADOTA, I, Y YAMAMOTO
TETRAHEDRON LETTERS 34 ( 8 ) 1313 - 1316 1993.2
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ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS VIA THE REACTION OF ALDEHYDES WITH CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANES
Y YAMAMOTO, K KOBAYASHI, H OKANO, KADOTA, I
JOURNAL OF ORGANIC CHEMISTRY 57 ( 26 ) 7003 - 7005 1992.12
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Diisopropyl Tartrate Modified (E)-gamma-[(Cyclohexyloxy)dimethylsilyl]- and (E)-gamma-(Dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective Synthesis of anti-1,2-Diols and 2-Butene-1,4-diols via the Formal alpha-・・・
Chemtracts: Org. Chem. 5 242 - 245 1992
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Diisopropyl Tartrate Modified (E)-gamma-[(Cyclohexyloxy)dimethylsilyl]- and (E)-gamma-(Dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective Synthesis of anti-1,2-Diols and 2-Butene-1,4-diols via the Formal alpha-・・・
Chemtracts: Org. Chem. 5 242 - 245 1992
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STEREOCONTROLLED INTRAMOLECULAR CYCLIZATION OF OMEGA-TRIBUTYLSTANNYL ETHER ALDEHYDES - SYNTHESIS OF THE 6.7.7.6 RING-SYSTEM OF POLYCYCLIC ETHERS
Y YAMAMOTO, J YAMADA, KADOTA, I
TETRAHEDRON LETTERS 32 ( 48 ) 7069 - 7072 1991.11
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SYNTHESIS OF BETA-ALKOXYCYCLIC ETHERS FROM OMEGA-ORGANOMETALLIC ETHER ACETALS - STEREOCONTROL WITH THE COMBINED LEWIS ACID SYSTEM, TITANIUM(IV) CHLORIDE-TRIPHENYLPHOSPHINE
KADOTA, I, GEVORGYAN, V, J YAMADA, Y YAMAMOTO
SYNLETT ,823-824 ( 11 ) 823 - 824 1991.11
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A NEW APPROACH TO THE CONSTRUCTION OF BETA-ALKOXY-SUBSTITUTED CYCLIC ETHERS VIA THE INTRAMOLECULAR CYCLIZATION OF OMEGA-TRIALKYLPLUMBYL AND OMEGA-TRIALKYLSTANNYL ETHER ACETALS
J YAMADA, T ASANO, KADOTA, I, Y YAMAMOTO
JOURNAL OF ORGANIC CHEMISTRY 55 ( 25 ) 6066 - 6068 1990.12
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H KOTSUKI, KADOTA, I, M OCHI
JOURNAL OF ORGANIC CHEMISTRY 55 ( 14 ) 4417 - 4422 1990.7
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H KOTSUKI, N YOSHIMURA, KADOTA, I, Y USHIO, M OCHI
SYNTHESIS-STUTTGART ,401-402 ( 5 ) 401 - 402 1990.5
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A SIMPLE AND EFFICIENT HETEROGENEOUS HYDROLYSIS OF N,N-DIMETHYLHYDRAZONE DERIVATIVES
H KOTSUKI, A MIYAZAKI, KADOTA, I, M OCHI
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ,429-430 ( 2 ) 429 - 430 1990.2
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AN EFFICIENT METHOD FOR THE ALKYLATION OF CHIRAL TRIFLATES WITH ALKYNYLLITHIUM REAGENTS - A HIGHLY CONCISE TOTAL SYNTHESIS OF (+)-PANAXACOL
H KOTSUKI, KADOTA, I, M OCHI
TETRAHEDRON LETTERS 31 ( 32 ) 4609 - 4612 1990
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H KOTSUKI, Y USHIO, KADOTA, I, M OCHI
JOURNAL OF ORGANIC CHEMISTRY 54 ( 21 ) 5153 - 5161 1989.10
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A NEW EXPEDITIOUS SYNTHESIS OF (+)-EXO-BREVICOMIN VIA EFFICIENT C-C BOND FORMATION OF TRIFLATES
H KOTSUKI, KADOTA, I, M OCHI
TETRAHEDRON LETTERS 30 ( 30 ) 3999 - 4000 1989
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A Novel Method for Copper(I)-Catalyzed Coupling Reactions of Triflates with Grignard Reagents
Tetrahedron Letters 30 ( 10 ) 1281 - 1284 1989
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A New Expeditious Synthesis of (+)-exo-Brevicomin via Efficient C-C Bond Formation of Triflutes
KOTSUKI H, KADOTA I, OCHI M
Tetrahedron Letters 30 ( 30 ) 3999 - 4000 1989
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A NOVEL METHOD FOR COPPER(I)-CATALYZED COUPLING REACTIONS OF TRIFLATES WITH GRIGNARD-REAGENTS
H KOTSUKI, KADOTA, I, M OCHI
TETRAHEDRON LETTERS 30 ( 10 ) 1281 - 1284 1989
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H KOTSUKI, Y USHIO, KADOTA, I, M OCHI
CHEMISTRY LETTERS ,927-930 ( 6 ) 927 - 930 1988.6
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PB90 STEREOSELECTIVE REDUCTION OF BICYCLIC KETALS : AN EFFICIENT ENTRY TO MEDIUM- AND LARGE-SIZED OXOCANE DERIVATIVES
Kotsuki Hiyoshizo, Ushio Yasuyuki, Kadota Isao, Ochi Masamitsu
International Symposium on the Chemistry of Natural Products 1988 336 1988
Awards
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日本化学会進歩賞
1998
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日本化学会若い世代の特別講演賞
1997
Research Projects
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海産毒シガトキシン類および海洋産マクロライド類の収束的全合成
Grant number：20K05496 2020.04 - 2023.03
日本学術振興会 科学研究費助成事業 基盤研究(C) 基盤研究(C)
門田 功
Grant amount：\4420000 （ Direct expense: \3400000 、 Indirect expense：\1020000 ）
本年度はでは、海産毒シガトキシンCTX3Cの全合成に向け、分子右側に位置するAB環部の大量合成について検討を行った。まずデオキシリボースを出発原料とし、これまでに行ってきた手順でのスケールアップを図ることで必要な量のフラグメント合成を行った。まだ目的のセグメント合成には至っていないが、途中いくつかのステップの改善も図ることができ、このまま順調に合成を進めることができれば必要な量の合成中間体を得ることができると考えている。
一方、THPマクロライドの合成研究に関しては、まず海洋産マクロライドであるマンデラライドAの全合成について検討した。この化合物はTHF環、THP環の2つのエーテル環を有するマクロライド骨格が特徴的であり、それらの立体選択的かつ収束的な合成が重要な課題となる。本年度は、四酸化オスミウムを触媒とするオレフィンとジオールとの立体選択的環化反応を用いることによってTHP環を立体選択的に構築し、その後ラクトンを還元的アセチル化によってα－アセトキシエーテルに変換した後、ルイス酸存在下で側鎖部分に対応するシリルエノールエーテルと反応させることで必要な側鎖部分を導入することができた。もう一つのTHP環部についても、同様の方法論を適用すべく、必要な基質を合成しているところである。
これらの研究と並行してもう一つの標的分子であるルーカスカンドロライAの合成研究についても検討している。この化合物においては、この化合物は2つのTHP環部を有する特異なマクロライド構造を有している。最終的に一方のTHP環を構築しながら全体のマクロライド骨格を合成するために、まずは一方のTHP環の立体選択的合成と側鎖変換をおこなっている。 -
Convergent Synthesis of Marine Natural Products by Using Intramolecular Allylation as a Key Step
Grant number：17K05863 2017.04 - 2020.03
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) Grant-in-Aid for Scientific Research (C)
Kadota Isao
Grant amount：\4810000 （ Direct expense: \3700000 、 Indirect expense：\1110000 ）
Both of the A-E and H-M ring segments of ciguatoxin 3C (CTX3C), a marine polycyclic ether, were synthesized via the intramolecular allylation followed by ring-closing metathesis, stereo-selectively. The segments synthesized were connected by esterification and subsequent ring-closing metathesis. Furthermore, the inter- and intramolecular double allylation protocol newly developed was successfully applied to the total synthesis of marine THP macrolides, dactylolide and enigmazole A.
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Grant number：25410118 2013.04 - 2016.03
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) Grant-in-Aid for Scientific Research (C)
KADOTA Isao, TAKAMURA Hiroyoshi
Grant amount：\5330000 （ Direct expense: \4100000 、 Indirect expense：\1230000 ）
Secondary metabolites produced by marine organism have been recognized as novel read compounds for new drag due to their potent bioactivities. However, because of the limited availability from nature, chemical synthesis has been required to obtain sufficient amounts of these compounds. Moreover, the unusual structures are particularly attractive targets for synthetic chemists. In this study, synthesis of these marine natural products was investigated by using convergent synthetic methodology based on intramolecular allylation.
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Synthetic Study of Ciguatoxin and Brevisin Based on Intramolecular Allylation
Grant number：22550036 2010 - 2012
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) Grant-in-Aid for Scientific Research (C)
KADOTA Isao
Grant amount：\4680000 （ Direct expense: \3600000 、 Indirect expense：\1080000 ）
In recent years there has been an explosion of interest in biologically active natural products of marine origin. Due to their structural novelty and toxicity, polycyclic ethers isolated from marine algae are particularly attractive targets for synthetic chemists. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of the polycyclic ethers. In this study, convergent synthesis of polycyclic ethers via the intramolecular allyaltion and ring-closing metathesis were examined.
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Efficient Synthesis of Marine Polycyclic Ethers
Grant number：19350023 2007 - 2009
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B) Grant-in-Aid for Scientific Research (B)
KADOTA Isao, TAKAMURA Hiroyoshi
Grant amount：\19110000 （ Direct expense: \14700000 、 Indirect expense：\4410000 ）
In recent years there has been an explosion of interest in biologically active natural products of marine origin. Due to their structural novelty and toxicity, polycyclic ethers isolated from marine algae are particularly attractive targets for synthetic chemists. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of the polycyclic ethers. In this study, convergent synthesis of brevenal and ciguatoxin CTX3C via the intramolecular allyaltion followed by ring-closing metathesis were examined.
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海洋産ポリ環状エーテルの高効率全合成
Grant number：15750075 2003 - 2005
日本学術振興会 科学研究費助成事業 若手研究(B) 若手研究(B)
門田 功
Grant amount：\3400000 （ Direct expense: \3400000 ）
昨年に引き続き、赤潮の原因毒であるブレベトキシンBの合成研究を行った。デオキシリボースを光学活性源として、BC環部に相当するα-クロロスルフィドとFG環部アルコールをそれぞれ合成した。両者を銀トリフレートを用いて縮合し、O,S-アセタールを合成した。さらに数段階でアリルスズを導入して分子内アリル化反応のための基質を合成した。この化合物を銀トリフレートで処理したところ84%の収率で環化反応が進行し、目的の化合物が立体選択的に得られてきた。得られた化合物に対し、Grubbs触媒による閉環メタセシスをおこなってB-G環セグメントを得ることができた。さらに数段階を経てA環を構築し、A-G環部とした。これをJK環部に相当するカルボン酸とエステル縮合し、さらに数段階を経て環化前駆体を合成した。この化合物に対して先ほどと同様に分子内アリル化と閉環メタセシスをおこない、ブレベトキシンBのポリエーテル骨格を得ることができた。この化合物に対してラクトン化、脱保護、アリルアルコールの選択的酸化を行い、ブレベトキシンBの全合成を完了した。合成品の各種スペクトルデータは天然のものと完全に一致した。
また、同様の方法論を用い、イェッソトキシンおよびアドリアトキシンのFGHI環部の収束的合成に成功した。これらの化合物は下痢性貝毒の原因毒として、二枚貝養殖に多きな被害を与えており、ブレベトキシンBと同様深刻な社会問題となっている。本研究により、これら海産毒の活性発現機構に関する研究が進展するものと期待される。 -
Development of Sustainable Process for Molecular Transformation Using Lewis Acid/Transition Metal Catalysts
Grant number：14002001 2002 - 2006
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Specially Promoted Research Grant-in-Aid for Specially Promoted Research
YAMAMOTO Yoshinori, ASAO Naoki, NAKAMURA Itaru, TIENAN Jin, KADOTA Isao
Grant amount：\585000000 （ Direct expense: \450000000 、 Indirect expense：\135000000 ）
Stereocontroll via σ-π chelation was achieved by using group 13 Lewis acids. During this study, we found that some palladium (II) species act not only as transition metal catalyst but also as Lewis acid catalyst. Based on this finding, total syntheses of natural products, BCH-2051 and vibsanol, were achieved. Furthermore, antibiotics, (+)-ochromycinoneand (+)-rubiginone B2, were synthesized by using novel Au catalyst.
Asymmetric allylation of imine derivatives was achieved by using optically active bis-π-allylpalladium, and the reaction was applied to the preparation of a synthetic intermediate of DMP-777. As a related reaction, novel synthetic method for cyanoindoles via three component coupling was developed. We found that the intramolecular reaction of amines and alkynes give nitrogen heterocycles in the presence of palladium/acetic acid catalyst. This reaction was applied to the total synthesis of an alkaloid, 209D.
α-Allylation of hetero-aromatics and ketones were achieved by using methylenecyclopropane and palladium catalyst. On the other hand, the reaction with methyleneaziridine provided pyrrole derivatives having a pyridine or benzene ring.
Total syntheses of marine polycyclic ethers, gambierol and brevetoxin B, were achieved via the intramolecular allylation followed by ring-closing metathesis. -
海洋産ポリ環状エーテルの合成研究
Grant number：12740337 2000 - 2001
日本学術振興会 科学研究費助成事業 奨励研究(A) 奨励研究(A)
門田 功
Grant amount：\2200000 （ Direct expense: \2200000 ）
まず、ガンビエロールのE環およびH環部の短段階合成について検討した。デオキシリボースから誘導した7員環ラクトンを定法によりケテンアセタールトリフレートとした。これに対し、パラジウム触媒依存下、亜鉛ホモエノレートを作用させることで対応するカップリング生成物を良好な収率で得ることに成功した。得られた生成物は、ハイドロボレーションおよびラクトン化によって、ガンビエロールE環部およびH環部へと変換することができた。今回用いた方法では、アリルスズを用いる従来法に比べて行程数を約3分の2に短縮することができた。次に各セグメントの連結についてのモデル実験を行った。カルボン酸とアルコールから合成したエステルに対し、脱保護、アセタール化、脱離を行いアリルスズを導入した。次にエステル部をDIBALHで還元した後、生じたアルミニウムヘミアセタールを無水酢酸でトラップし、αーアセトキシエーテルを合成した。同様の方法で様々な環化前駆体を合成し、ルイス酸による環化反応を検討した。反応はどの場合も収率良く進行し、目的の化合物が立体選択的に得られてきた。次に得られたジエンに対し、ルテニウム触媒を用いる閉環メタセシスを検討した。この場合も反応は収率良く進行し、様々な大きさのポリ環状エーテルを得ることができた。また、同様の方法論を用いることで、ガンビエロールのCDEFG環部の合成にも成功した。
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海洋産ポリ環状エーテルの合成研究
Grant number：11740341 1999
日本学術振興会 科学研究費助成事業 奨励研究(A) 奨励研究(A)
門田 功
Grant amount：\1400000 （ Direct expense: \1400000 ）
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海産毒ガンビエロールの合成研究
Grant number：09740538 1997 - 1998
日本学術振興会 科学研究費助成事業 奨励研究(A) 奨励研究(A)
門田 功
Grant amount：\2100000 （ Direct expense: \2100000 ）
海産毒ガンビエロールの全合成研究の一環として、AB環、E環、およびH環部の合成を行った。まず、2-deoxy-D-riboseを光学活性源とし、文献記載の方法でB環部に相当する部分を合成した。この化合物に対し、キラルなアリルボランを作用させ、目的のアリル化体をほぼ単一物として得ることができた。さらに分子内ヘテロマイケル反応によって環化を行い、AB環の合成に成功した。7員環エーテルであるE環部は、アリルスズとアルデヒドとの分子内反応を用いて合成した。すなわち、D-riboseから数段階で環化前駆体を合成し、ルイス酸を作用させることにより、高収率で目的のE環部を合成することができた。このとき、かなりの割合で立体異性体が得られてきたが、数段階の操作で目的物に変換することができた。H環部についても同様の方法論を用いた。すなわち、2-deoxy-D-riboseから出発し、アリルスズとアルデヒドとの分子内反応を用いて7員環を合成した。このときには他の立体異性体は全く得られず、目的物のみが単一物として得られてきた。環内に二重結合とメチル基を立体選択的に導入した後、パラジウム触媒による有機スズ化合物とのカップリング反応によって側鎖のトリエン部を構築し、H環部を合成することができた。現在、この様にして合成した各セグメントの連結について検討中である。
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New Synthetic Method for Chiral B-Lactams
Grant number：07044305 1995
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for International Scientific Research. Grant-in-Aid for International Scientific Research.
YAMAMOTO Yoshinori, GYOUNG Young Soo, NAKAMURA Hiroyuki, KADOTA Isao, ASAO Naoki, NEMOTO Hisao
Amide cuprate reagents, (R_2N)_2CuLi and higher order cyano cuprates (R_2N)_2Cu(CN)Li_2, have been developed as a new class of nitrogen nucleophiles. These reagents underwent regioselective 1,4-addition to alpha, beta, gamma, delta-dienoates whereas R_2NH gave a 1,6-addition product and the lithium reagent R_2NLi afforded a mixture of 1,4-and 1,2-addition products. The amide cuprates were added to chiral alpha, beta, gamma, delta-dienoates having a 8-phenylmenthyl or bornanesultam chiral auxiliary to produce 1,4-adducts in good to high diastereoselectivity. The addition of [BnN(TMS)]_2CuLi and [BnN(TMS)]_2Cu(CN)Li_2 to 8-phenylmenthyl 5-phenyl-2,4-pentadienoate or 5-phenyl-2,4-pentadienoylbornanesultam produced (R) -chirality at the beta-position. The 1,4-addition of [BnN(TMS)]_2Cu(CN)Li_2 to the bornanesultam followed by trapping withacetaldehyde gave the alpha-(1-hydroxyethyl)-beta-amino derivative as a single isomer in good yield. This three component coupling was used in an asymmetric synthesis of a beta-lactam.
Conjugate addition of N-benzyl-N-((R)-1-Phenylethyl)amine to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate produced the (3S,4R)-syn-adduct with essentially 100% de in 84% yield, whereas the addition of (S)-amine to the pentenoate afforded the (3R,4R) -anti-adduct with essentially 100% de in 95% yield. The syn adduct was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate ; the diastereoisomer ratio of the key intermediate : the diastereoisomer ratio of the key intermediate to other diasteroisomers was 80 : 20. Conversion to a 1beta-methylcarbapenem key intermediate was carried out readily according to the known procedures. -
海産毒ヘミブレベトキシンBの合成とその生理活性に関する研究
Grant number：07740483 1995
日本学術振興会 科学研究費助成事業 奨励研究(A) 奨励研究(A)
門田 功
Grant amount：\800000 （ Direct expense: \800000 ）
海洋産のポリエーテル系天然物であるヘミブレベトキシンBの合成研究を行った。この化合物は赤潮の原因毒の一つとして渦鞭毛藻の一種Gymnodinium breveから単離された四環性の化合物である。興味深いことにこの魚毒成分は海産ポリエーテルに共通する神経毒性以外に腫瘍細胞に対する活性を示すことが知られており、医薬品への応用も期待されている。本研究では光学活性なd-マンノースから出発し、有機スズ化合物とアルデヒドとの分子内環化反応を利用することによって、ポリエーテル骨格を構築するというルートをとった。その結果、ヘミブレベトキシンBに含まれる四つのエーテル環を全て高立体選択的に合成することに成功した。続いて既知法によって二つの側鎖を導入し、全合成を完了した。今後更に検討を続け、この天然物の大量供給法を確立する。また、その生理活性について詳細な調査を実施し、活性発現機構など生体内での動的挙動についての研究を行う予定である。
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海洋産ポリエーテル系天然物の合成研究
Grant number：06740545 1994
日本学術振興会 科学研究費助成事業 奨励研究(A) 奨励研究(A)
門田 功
Grant amount：\900000 （ Direct expense: \900000 ）
海洋産のポリエーテル系天然物であるヘミブレべトキシンB(1)の合成研究を行った。この化合物は赤潮の原因毒の一つとして渦鞭毛藻の一種Gymnodinium breveから単離された四環性の化合物である。興味深いことにこの魚毒成分は海産ポリエーテルに共通する神経毒性以外に腫瘍細胞に対する活性を示すことが知られており、医薬品への応用も期待されている。本研究では光学活性なd-マンノース2から出発し、有機スズ化合物の分子内環化反応を利用することによって、ポリエーテル骨格を構築するというルートをとった。その結果、ヘミブレベトキシンBに含まれる四つのエーテル環を有する化合物3を高立体選択的に合成することに成功した。今後さらに研究を続け、残る測鎖の導入を行いこの天然物の全合成を目指す。また、合成完了時にはその生理活性についてさらに詳細な調査を実施し、活性発現機構など生体内での動的挙動についての研究を行う予定である。また天然物そのものに対して各種の化学修飾を施し、その生理活性を調べることによって海洋産ポリエーテルの構造活性相関についての研究も行う。
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