研究者詳細 - 坂倉　彰

Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers 査読

Visible-Light-Photoexcited Palladium-Catalyzed Silylmethylation of Benzyl Alcohol Derivatives 招待査読

Haruki Mizoguchi, Akira Sakakura, Ryuji Yoshida, Haruka Ikeda

Synlett 34 ( 20 ) 2451 - 2454 2023年7月

Enantioselective construction of beta-hydroxy-alpha,alpha-disubstituted alpha-amino acid derivatives via direct aldol reaction of alpha-imino esters 査読

Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura

TETRAHEDRON 110 2022年3月

Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement 査読

Haruki Mizoguchi, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida, Akira Sakakura

Chemical Science 13 ( 33 ) 9580 - 9585 2022年

Ichiro Hayakawa, Naochika Matsumaru, Akira Sakakura

The Journal of Organic Chemistry 86 ( 14 ) 9802 - 9810 2021年7月

Strain-release Difunctionalization of C–C σ- and π-bonds of an Organoboron Ate-complex through 1,2-Metallate Rearrangement 招待査読

Haruki Mizoguchi, Akira Sakakura

Chemistry Letters 50 ( 4 ) 792 - 799 2021年4月

Dual Inhibition of γ-Tubulin and Plk1 Induces Mitotic Cell Death 査読

Haruna Ebisu, Kana Shintani, Takumi Chinen, Yoko Nagumo, Shuya Shioda, Taisei Hatanaka, Akira Sakakura, Ichiro Hayakawa, Hideo Kigoshi, Takeo Usui

Frontiers in Pharmacology 11 2021年1月

掲載種別：研究論文（学術雑誌）出版者・発行元：Frontiers Media SA

α/β-Tubulin inhibitors that alter microtubule (MT) dynamics are commonly used in cancer therapy, however, these inhibitors also cause severe side effects such as peripheral neuropathy. γ-Tubulin is a possible target as antitumor drugs with low side effects, but the antitumor effect of γ-tubulin inhibitors has not been reported yet. In this study, we verified the antitumor activity of gatastatin, a γ-tubulin specific inhibitor. The cytotoxicity of gatastatin was relatively weak compared with that of the conventional MT inhibitors, paclitaxel and vinblastine. To improve the cytotoxicity, we screened the chemicals that improve the effects of gatastatin and found that BI 2536, a Plk1 inhibitor, greatly increases the cytotoxicity of gatastatin. Co-treatment with gatastatin and BI 2536 arrested cell cycle progression at mitosis with abnormal spindles. Moreover, mitotic cell death induced by the combined treatment was suppressed by the Mps1 inhibitor, reversine. These findings suggest that co-treatment with Plk1 and γ-tubulin inhibitors causes spindle assembly checkpoint-dependent mitotic cell death by impairing centrosome functions. These results raise the possibility of Plk1 and γ-tubulin inhibitor co-treatment as a novel cancer chemotherapy.

DOI： 10.3389/fphar.2020.620185

Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester–Amide Exchange Reaction 査読

Akira Sakakura, Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi

Synlett 31 ( 20 ) 2018 - 2022 2020年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

<title>Abstract</title>
C
1-Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester–amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k
fast/k
slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

DOI： 10.1055/s-0040-1707303

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts 査読

Akira Sakakura, Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi

Synlett 31 ( 20 ) 2013 - 2017 2020年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

<title>Abstract</title>An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C
1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

DOI： 10.1055/s-0040-1707302

Structure Optimization of Gatastatin for the Development of gamma-Tubulin-Specific Inhibitor 査読

Kana Shintani, Haruna Ebisu, Minagi Mukaiyama, Taisei Hatanaka, Takumi Chinen, Daisuke Takao, Yoko Nagumo, Akira Sakakura, Ichiro Hayakawa, Takeo Usui

ACS MEDICINAL CHEMISTRY LETTERS 11 ( 6 ) 1125 - 1129 2020年6月

Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction 査読

Yuya Araki, Natsumi Miyoshi, Kazuki Morimoto, Takayuki Kudoh, Haruki Mizoguchi, Akira Sakakura

JOURNAL OF ORGANIC CHEMISTRY 85 ( 2 ) 798 - 805 2020年1月

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate 査読

Haruki Mizoguchi, Masaya Seriu, Akira Sakakura

Chemical Communications 56 ( 99 ) 15545 - 15548 2020年

Toward the Synthesis of SB-203207: Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers 査読

Ichiro Hayakawa, Anna Nagayasu, Akira Sakakura

The Journal of Organic Chemistry 84 ( 23 ) 15614 - 15623 2019年12月

Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts 査読

Chihiro Kidou, Haruki Mizoguchi, Tatsuo Nehira, Akira Sakakura

Synlett 30 ( 15 ) 1835 - 1839 2019年9月

Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine 査読国際誌

Ichiro Hayakawa, Ryosuke Nagatani, Masaki Ikeda, Dong-eun Yoo, Keita Saito, Hideo Kigoshi, Akira Sakakura

Organic Letters 21 ( 16 ) 6337 - 6341 2019年8月

Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives 査読

Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura

Organic Letters 21 ( 7 ) 2073 - 2076 2019年4月

Catalytic enantioselective Hosomi–Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes 査読

Yutaro Niwa, Mayu Miyake, Ichiro Hayakawa, Akira Sakakura

Chemical Communications 55 ( 27 ) 3923 - 3926 2019年

Chiral Pyrophosphoric Acid Catalysts for the para-Selective and Enantioselective Aza-Friedel–Crafts Reaction of Phenols 査読

Akira Sakakura, Manabu Hatano, Kazuaki Ishihara, Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji

Synthesis 50 ( 23 ) 4577 - 4590 2018年12月

Enantioselective aza-Friedel–Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts 査読

Manabu Hatano, Haruka Okamoto, Taro Kawakami, Kohei Toh, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Chemical Science 9 ( 30 ) 6361 - 6367 2018年

Regioselective DMAD-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions 査読

Ichiro Hayakawa, Yuji Yamanaka, Koichi Mitsudo, Hiromi Ota, Akira Sakakura

Heterocycles 94 ( 12 ) 2299 - 2306 2017年12月

Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C 査読

Takayuki Kudoh, Yuya Araki, Natsumi Miyoshi, Mizuho Tanioka, Akira Sakakura

ASIAN JOURNAL OF ORGANIC CHEMISTRY 6 ( 12 ) 1760 - 1763 2017年12月

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels–Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles 査読

Takayuki Kudoh, Syo Fujisawa, Megumi Kitamura, Akira Sakakura

Synlett 28 ( 16 ) 2189 - 2193 2017年10月

Reinvestigation of the Biomimetic Cyclization of 3,5-Diketoesters: Application to the Total Synthesis of Cyercene A, an α-Methoxy-γ-Pyrone-Containing Polypropionate 査読

Kai Onda, Ichiro Hayakawa, Akira Sakakura

Synlett 28 ( 13 ) 1596 - 1600 2017年8月

Discovery of O6-benzyl glaziovianin A, a potent cytotoxic substance and a potent inhibitor of α,β-tubulin polymerization 査読

Ichiro Hayakawa, Shuya Shioda, Takumi Chinen, Taisei Hatanaka, Haruna Ebisu, Akira Sakakura, Takeo Usui, Hideo Kigoshi

Bioorganic and Medicinal Chemistry 24 ( 21 ) 5639 - 5645 2016年11月

A short access to 3,5-disubstituted piperazinones based on the aza-Michael addition of α-amino esters to β-substituted nitroalkenes 査読

Takayuki Kudoh, Seiji Isoyama, Sachiko Kagimoto, Katsutoshi Kurihara, Akira Sakakura

Tetrahedron Letters 57 ( 42 ) 4693 - 4696 2016年10月

Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts 査読

Yasuhiro Sawamura, Yoshihiro Ogura, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

CHEMICAL COMMUNICATIONS 52 ( 36 ) 6068 - 6071 2016年

Stereoselective Electrophilic Cyclization 査読

Akira Sakakura, Kazuaki Ishihara

CHEMICAL RECORD 15 ( 4 ) 728 - 742 2015年8月

Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Propioloylpyrazoles Induced by Chiral π-Cation Catalysts 査読

Masahiro Hori, Akira Sakakura, Kazuaki Ishihara

Journal of the American Chemical Society 136 ( 38 ) 13198 - 13201 2014年9月

Selective Bromocyclization of 2-Geranylphenols Promoted by Phosphite-Urea Cooperative Catalysts 査読

Yasuhiro Sawamura, Hidefumi Nakatsuji, Matsujiro Akakura, Akira Sakakura, Kazuaki Ishihara

CHIRALITY 26 ( 7 ) 356 - 360 2014年7月

Cooperative Activation with Chiral Nucleophilic Catalysts and N-Haloimides: Enantioselective Iodolactonization of 4-Arylmethyl-4-pentenoic Acids 査読

Hidefumi Nakatsuji, Yasuhiro Sawamura, Akira Sakakura, Kazuaki Ishihara

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 ( 27 ) 6974 - 6977 2014年7月

Catalytic Enantioselective Inverse Electron Demand Hetero-Diels-Alder Reaction with Allylsilanes 査読

Yuki Matsumura, Takahiro Suzuki, Akira Sakakura, Kazuaki Ishihara

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 ( 24 ) 6131 - 6134 2014年6月

Enantioselective Cyanoethoxycarbonylation of Isatins Promoted by a Lewis Base–Brønsted Acid Cooperative Catalyst 査読

Yoshihiro Ogura, Matsujiro Akakura, Akira Sakakura, Kazuaki Ishihara

Angewandte Chemie International Edition 52 ( 32 ) 8299 - 8303 2013年8月

Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative Amide Condensation of α-Hydroxycarboxylic Acids 査読

Risa Yamashita, Akira Sakakura, Kazuaki Ishihara

Organic Letters 15 ( 14 ) 3654 - 3657 2013年7月

Kinetic Resolution of Racemic Carboxylic Acids through Asymmetric Protolactonization Promoted by Chiral Phosphonous Acid Diester 査読

Masayuki Sakuma, Akira Sakakura, Kazuaki Ishihara

ORGANIC LETTERS 15 ( 11 ) 2838 - 2841 2013年6月

“Phosphite–Urea” Cooperative High-Turnover Catalysts for the Highly Selective Bromocyclization of Homogeranylarenes 査読

Yasuhiro Sawamura, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Chemical Science 4 ( 11 ) 4181 - 4186 2013年

α-Heterosubstituted β-Alkylacroleins as Useful Multisubstituted Dienophiles for Enantioselective Diels-Alder Reactions 査読

Akira Sakakura, Hiroki Yamada, Kazuaki Ishihara

Asian Journal of Organic Chemistry 1 ( 2 ) 133 - 137 2012年10月

Enantioselective Diels–Alder Reaction of α-(Acylthio)acroleins: a New Entry to Sulfur-containing Chiral Quaternary Carbons 査読

Akira Sakakura, Hiroki Yamada, Kazuaki Ishihara

Organic Letters 14 ( 12 ) 2972 - 2975 2012年6月

N,N-Diarylammonium Pyrosulfate as a Highly Effective Reverse Micelle-Type Catalyst for Hydrolysis of Esters 査読

Yoshiki Koshikari, Akira Sakakura, Kazuaki Ishihara

ORGANIC LETTERS 14 ( 12 ) 3194 - 3197 2012年6月

Hydrophobic N,N-Diarylammonium Pyrosulfates as Dehydrative Condensation Catalysts under Aqueous Conditions 査読

Akira Sakakura, Yoshiki Koshikari, Matsujiro Akakura, Kazuaki Ishihara

ORGANIC LETTERS 14 ( 1 ) 30 - 33 2012年1月

Aplyronines D–H from the sea hare Aplysia kurodai: isolation, structures, and cytotoxicity 査読

Makoto Ojika, Hideo Kigoshi, Kiyotake Suenaga, Yoshifumi Imamura, Kohji Yoshikawa, Takeshi Ishigaki, Akira Sakakura, Tsuyoshi Mutou, Kiyoyuki Yamada

Tetrahedron 68 ( 4 ) 982 - 987 2012年1月

Desymmetrization of meso-Glycerol Derivatives Induced by L-Histidine-Derived Acylation Catalysts 査読

Akira Sakakura, Shuhei Umemura, Kazuaki Ishihara

ADVANCED SYNTHESIS & CATALYSIS 353 ( 11-12 ) 1938 - 1942 2011年8月

Chiral Lewis Base-Assisted Brønsted Acid (LBBA)-Catalyzed Enantioselective Cyclization of 2-Geranylphenols 査読

Akira Sakakura, Masayuki Sakuma, Kazuaki Ishihara

Organic Letters 13 ( 12 ) 3130 - 3133 2011年6月

Brønsted Base-Assisted Boronic Acid Catalysis for the Dehydrative Intramolecular Condensation of Dicarboxylic Acids 査読

Akira Sakakura, Takuro Ohkubo, Risa Yamashita, Matsujiro Akakura, Kazuaki Ishihara

Organic Letters 13 ( 5 ) 892 - 895 2011年3月

Intramolecular Dehydrative Condensation of Dicarboxylic Acids with Brønsted Base-Assisted Boronic Acid Catalysts 査読

Akira Sakakura, Risa Yamashita, Takuro Ohkubo, Matsujiro Akakura, Kazuaki Ishihara

Australian Journal of Chemistry 64 ( 11 ) 1458 - 1465 2011年

Asymmetric Cu(II) catalyses for cycloaddition reactions based on π–cation or n–cation interaction 査読

Akira Sakakura, Kazuaki Ishihara

Chemical Society Reviews 40 ( 1 ) 163 - 172 2011年

Nucleophilic Phosphine–Catalyzed Iodocyclization of Isoprenoids Bearing an Oxygen Terminal Group 査読

Akira Sakakura, Gakujun Shomi, Atsushi Ukai, Kazuaki Ishihara

Heterocycles 82 ( 1 ) 249 - 255 2010年12月

Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Nitrones with Propioloylpyrazoles and Acryloylpyrazoles Induced by Chiral π–Cation Catalysts 査読

Akira Sakakura, Masahiro Hori, Makoto Fushimi, Kazuaki Ishihara

Journal of the American Chemical Society 132 ( 44 ) 15550 - 15552 2010年11月

ChemInform Abstract: Jolkinolide D Pharmacophore: Synthesis and Reaction with Amino Acids, Nucleosides, and DNA.

Akira Sakakura, Yui Takayanagi, Hideo Kigoshi

ChemInform 33 ( 46 ) no - no 2010年5月

Organoammonium Salt-Catalyzed Enantioselective Cycloaddition Reactions with α-(Acyloxy)- or α-Diacylaminoacroleins 査読

Akira Sakakura, Kazuaki Ishihara

Bulletin of the Chemical Society of Japan 83 ( 4 ) 313 - 322 2010年4月

Rational Design of Highly Effective Asymmetric Diels-Alder Catalysts Bearing 4,4 '-Sulfonamidomethyl Groups 査読

Akira Sakakura, Rei Kondo, Yuki Matsumura, Matsujiro Akakura, Kazuaki Ishihara

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 131 ( 49 ) 17762 - 17764 2009年12月

3-Pyrroline-1-carbonyl (Pyroc) Group: A Removable Protecting Group for the Kinetic Resolution of Racemic Carboxylic Acids and Alcohols through Catalytic Asymmetric Acylation 査読

Akira Sakakura, Shuhei Umemura, Kazuaki Ishihara

SYNLETT ( 10 ) 1647 - 1650 2009年6月

Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds 査読

Akira Sakakura, Rei Kondo, Shuhei Umemura, Kazuaki Ishihara

TETRAHEDRON 65 ( 10 ) 2102 - 2109 2009年3月

Design of High-Performance Catalysts Based on Acid-Base Combined Salts and Development of Highly Selective Reactions 査読

Akira Sakakura

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 66 ( 10 ) 942 - 952 2008年10月

SELECTIVE SYNTHESIS OF CYCLIC PHOSPHORIC ACID DIESTERS THROUGH OXORHENIUM(VII)-CATALYZED DEHYDRATIVE CONDENSATION OF PHOSPHORIC ACID WITH ALCOHOLS 査読

Akira Sakakura, Masayuki Sakuma, Mikimoto Katsukawa, Kazuaki Ishihara

HETEROCYCLES 76 ( 1 ) 657 - 665 2008年9月

Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction 査読

Kazuaki Ishihara, Yuji Kosugi, Shuhei Umemura, Akira Sakakura

ORGANIC LETTERS 10 ( 15 ) 3191 - 3194 2008年8月

Open-air and solvent-free ester condensation catalyzed by sulfonic acids 査読

Akira Sakakura, Yoshiki Koshikari, Kazuaki Ishihara

TETRAHEDRON LETTERS 49 ( 34 ) 5017 - 5020 2008年8月

Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones 査読

Akira Sakakura, Hitoshi Watanabe, Kazuaki Ishihara

ORGANIC LETTERS 10 ( 12 ) 2569 - 2572 2008年6月

Convergent total syntheses of fluvibactin and vibriobactin using molybdenum(VI) oxide-catalyzed dehydrative cyclization as a key step 査読

Akira Sakakura, Shuhei Umemura, Kazuaki Ishihara

CHEMICAL COMMUNICATIONS ( 30 ) 3561 - 3563 2008年

Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions 査読

Akira Sakakura, Kirnio Kawajiri, Takuro Ohkubo, Yuji Kosugi, Kazuaki Ishihara

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129 ( 47 ) 14775 - 14779 2007年11月

Enantioselective biomimetic polyene cyclization of polyprenoids - Long-sought enantioselective reaction induced by a "chiral halonium ion" 査読

Akira Sakakura, Kazuaki Ishihara

CHIMICA OGGI-CHEMISTRY TODAY 25 ( 5 ) 9 - 12 2007年9月

Catalytic synthesis of peptide-derived thiazolines and oxazolines using Bis(quinolinolato)dioxomolybdenum(VI) complexes 査読

Akira Sakakura, Rei Kondo, Shuhei Umemura, Kazuaki Ishihara

ADVANCED SYNTHESIS & CATALYSIS 349 ( 10 ) 1641 - 1646 2007年7月

Dehydrative cyclization catalyzed by the combination of molybdenum(VI) oxides and benzoic acids: First synthesis of the antitumour substance BE-70016 査読

Akira Sakakura, Shuhei Umemura, Rei Kondo, Kazuaki Ishihara

ADVANCED SYNTHESIS & CATALYSIS 349 ( 4-5 ) 551 - 555 2007年3月

Design of highly functional small-molecule catalysts and related reactions based on acid-base combination chemistry 査読

Kazuaki Ishihara, Akira Sakakura, Manabu Hatano

SYNLETT ( 5 ) 686 - 703 2007年3月

Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites 査読

Akira Sakakura, Atsushi Ukai, Kazuaki Ishihara

NATURE 445 ( 7130 ) 900 - 903 2007年2月

Unusual rate acceleration in bronsted acid catalyzed dehydration reactions: Local hydrophobic environment in aggregated N-(2,6-diphenylphenyl)-N-mesitylammonium pentafluorobenzenesulfonates 査読

Akira Sakakura, Hitoshi Watanabe, Shoko Nakagawa, Kazuaki Ishihara

CHEMISTRY-AN ASIAN JOURNAL 2 ( 4 ) 477 - 483 2007年

Direct ester condensation catalyzed by bulky diarylammonium pentafluorobenzenesulfonates 査読

Akira Sakakura, Shoko Nakagawa, Kazuaki Ishihara

NATURE PROTOCOLS 2 ( 7 ) 1746 - 1751 2007年

Bulky phosphazenium cation catalysis for dehydrative condensation of phosphoric acid with alcohols 査読

Akira Sakakura, Mikimoto Katsukawa, Takaomi Hayashi, Kazuaki Ishihara

GREEN CHEMISTRY 9 ( 11 ) 1166 - 1169 2007年

The oxorhenium(VII)-catalyzed direct condensation of phosphoric acid with an alcohol 査読

Akira Sakakura, Mikimoto Katsukawa, Kazuaki Ishihara

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 46 ( 9 ) 1423 - 1426 2007年

Enantioselective Diels-Alder reaction of alpha-acyloxyacroleins catalyzed by chiral 1,1 '-binaphthyl-2,2 '-diammonium salts 査読

Akira Sakakura, Kenji Suzuki, Kazuaki Ishihara

ADVANCED SYNTHESIS & CATALYSIS 348 ( 16-17 ) 2457 - 2465 2006年11月

35 細胞毒性マクロリド配糖体、オーリサイド類の合成(口頭発表の部)

末永聖武, 星野紘史, 好井孝典, 森和規, 曽根大紀, 別所祐紀, 坂倉彰, 早川一郎, 山田靜之, 木越英夫

天然有機化合物討論会講演要旨集 ( 48 ) 205 - 210 2006年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Aurisides A (1) and B (2) are macrolide glycosides isolated from Japanese sea hare Dolabella auricuralia, which exhibit cytotoxicity against HeLa S_3 cells with IC_<50> values of 0.17 and 1.2μg/mL, respectively. The main structural features of aurisides are a bromine-substituted conjugated diene, a 14-membered lactone, and a cyclic hemiacetal. We achieved the enantioselective synthesis of aurisides A and B by a convergent approach. The C1-C9 segment 4 was prepared from (R)-pantolactone using a reaction of dithiane carbanion with epoxide, stereoselective reduction of β-hydroxyketone with Me_4NBHOAc, and rhodium-catalyzed Reformatsky-type reaction as key steps. The C10-C17 segment 12 was synthesized from (R)-glycidyl trityl ether. The Nozaki-Hiyama-Kishi reaction between 4 and 12 and subsequent reactions including construction of bromine-substituted conjugated diene gave seco acid 10, which was converted into the aglycon (3) of aurisides by construction of the 14-membered lactone. The Mukaiyama glycosylation reaction of the aglycon 3 provided aurisides A (1) and B (2).

DOI： 10.24496/tennenyuki.48.0_205

8 海洋産抗腫瘍性化合物アプリロニンAの抗腫瘍機序(口頭発表の部)

黒田武史, 末永聖武, 半田知久, 宮沙織, 岡本和人, 兼松憲吾, 坂倉彰, 山田靜之, 平田邦生, 高田昌樹, 加藤健一, 村岡真, 山本雅貴, 田中宏志, 木越英夫

天然有機化合物討論会講演要旨集 ( 48 ) 43 - 48 2006年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

The interaction between actin and aplyronine A, a potent antitumor and actin-depolymerizing substance of marine origin, was investigated by photoaffinity labeling experiments and X-ray structure analysis of actin complex with aplyronine A. Photoaffinity probes consisting of a side-chain portion of aplyronine A as a ligand, a diazirine moiety as a photoaffinity group, and a fluorophor as a detecting group were synthesized. Photolabeling experiments between actin and the probe were carried out. Actin was successfully photolabeled by the fluorescent probe and visualized clearly. The present results provide the first chemical evidence for the direct interaction between actin and the side-chain portion of aplyronine A. X-ray structure analysis of actin-aplyronine A complex was carried out. The analysis showed that Aplyronine A bound to a hydrophobic cleft between subdomains 1 and 3 of actin. The structural feature is that the trimethylserine moiety protrudes toward the bulk solvent region.

DOI： 10.24496/tennenyuki.48.0_43

Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin 査読

Kiyotake Suenaga, Hiroshi Hoshino, Takanori Yoshii, Kazunori Mori, Hiroki Sone, Yuhki Bessho, Akira Sakakura, Ichiro Hayakawa, Kiyoyuki Yamada, Hideo Kigoshi

TETRAHEDRON 62 ( 33 ) 7687 - 7698 2006年8月

Synthesis and biological activity of mycalolide analogs 査読

Kiyotake Suenaga, Tomoyuki Kimura, Takeshi Kuroda, Keita Matsui, Saori Miya, Satomi Kuribayashi, Akira Sakakura, Hideo Kigoshi

TETRAHEDRON 62 ( 35 ) 8278 - 8290 2006年8月

P-81 ENANTIOSELECTIVE POLYENE HALOCYCLIZATION INDUCED BY NUCLEOPHILIC CHIRAL PHOSPHINES

Sakakura Akira, Ukai Atsushi, Ishihara Kazuaki

International Symposium on the Chemistry of Natural Products 2006 "P - 81" 2006年7月

Development of environmentally benign catalytic dehydration process 査読

Akira Sakakura, Kazuaki Ishihara

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 64 ( 6 ) 651 - 663 2006年6月

Chiral 1,1 '-binaphthyl-2,2 '-diammonium salt catalysts for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins 査読

Akira Sakakura, Kenji Suzuki, Kazuhiko Nakano, Kazuaki Ishihara

ORGANIC LETTERS 8 ( 11 ) 2229 - 2232 2006年5月

Study of the interaction between actin and antitumor substance aplyronine A with a novel fluorescent photoaffinity probe 査読

Takeshi Kuroda, Kiyotake Suenaga, Akira Sakakura, Tomohisa Handa, Kazuhito Okamoto, Hideo Kigoshi

Bioconjugate Chemistry 17 ( 2 ) 524 - 529 2006年3月

Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts 査読

Akira Sakakura, Shoko Nakagawa, Kazuaki Ishihara

Tetrahedron 62 ( 2-3 ) 422 - 433 2006年1月

P-12 酸化モリブデン触媒を用いる脱水環化反応によるオキサゾリン、チアゾリンの効率的合成(ポスター発表の部)

坂倉彰, 近藤玲, 梅村周平, 石原一彰

天然有機化合物討論会講演要旨集 ( 47 ) 475 - 480 2005年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Oxazoline, oxazole, thiazoline, and thiazole rings are important constituents of numerous bioactive natural products and pharmaceuticals. The biosynthesis of many naturally occurring oxazolines and thiazolines appears to involve the dehydrative cyclization of serine, threonine, and cysteine residues. Oxazoles and thiazoles are synthesized by the oxidation of oxazolines and thiazolines, respectively. We describe here a biomimetic synthesis of oxazolines and thiazolines catalyzed by molybdenum (IV or VI) oxides, their mode of cyclization is retentive at the β-position. In the course of screening various metal oxides as catalysts for the dehydrative cyclization of dipeptides 1a and 1b, we found that molybdenum oxides had good catalytic activities. Interestingly, the ammonium salts of molybdenum(VI) oxides, (NH_4)_6Mo_7O_<24>・4H_2O and (NH_4)_2MoO_4, exhibited remarkable catalytic activities and gave oxazolines 2a and 2b in a short reaction time, along with small amounts of 3a and 3b. Next, we examined the dehydrative cyclization of cysteine derivatives 4a and 4b to thiazolines 5a and 5b using molybdenum oxides as catalysts. In the case of the dehydrative cyclization of 4a, (NH_4)_6Mo_7O_<24>・4H_2O, (NH_4)_2MoO_4 and MoO_2(acac)_2 showed excellent catalytic activities. MoO_2(acac)_2 could catalyze the dehydrative cyclization of 4b, to give 5b in 70% yield along with 5c (15%). To the best of our knowledge, this is the first example of the catalytic dehydrative cyclization of dipeptide substrates that include serine, threonine, and cysteine residues. A key synthetic intermediate 11 of hennoxazole A and bis(oxazoline)s 13a and 13b were synthesized by the dehydrative cyclization using molybdenum oxide catalysts. In addition, polyaniline-supported MoO_2(acac)_2 could easily be recovered and reused.

DOI： 10.24496/tennenyuki.47.0_475

Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases 査読

Akira Sakakura, Mikimoto Katsukawa, Kazuaki Ishihara

Organic Letters 7 ( 10 ) 1999 - 2002 2005年5月

Molybdenum oxides as highly effective dehydrative cyclization catalysts for the synthesis of oxazolines and thiazolines 査読

Akira Sakakura, Rei Kondo, Kazuaki Ishihara

Organic Letters 7 ( 10 ) 1971 - 1974 2005年5月

Bulky diarylammonium arenesulfonates as selective esterification catalysts 査読

Kazuaki Ishihara, Shoko Nakagawa, Akira Sakakura

Journal of the American Chemical Society 127 ( 12 ) 4168 - 4169 2005年3月

Formal synthesis of optically active ingenol via ring-closing olefin metathesis 査読

Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, Hideo Kigoshi

Journal of Organic Chemistry 69 ( 23 ) 7802 - 7808 2004年11月

Spongiacysteine, a novel cysteine derivative from marine sponge Spongia sp. 査読

Keiko Kobayashi, Hiroki Shimogawa, Akira Sakakura, Toshiaki Teruya, Kiyotake Suenaga, Hideo Kigoshi

Chemistry Letters 33 ( 10 ) 1262 - 1263 2004年10月

99(P-32) 光学活性インゲノールの合成(ポスター発表の部)

渡邉和志, 鈴木佑人, 青木健太, 坂倉彰, 末永聖武, 木越英夫

天然有機化合物討論会講演要旨集 ( 46 ) 569 - 574 2004年10月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Ingenol is a diterpenoid isolated from Euphorbia ingens, possessing a bicyclo[4.4.1]undecane skeleton with a highly strained inside, outside-intrabridgehead stereochemistry. Several strategies for construction of the unique skeleton have been reported, however, direct cyclization to the inside, ousidet-bicyclo[4.4.1]undecane system has not been reported. Recently, two total syntheses in a racemic form using the aforementioned strategies were reported by Winkler and Tanino-Kuwajima. We would like to report the construction of strained carbon skeletons of ingenol by direct cyclization with ring-closing olefin metathesis (RCM). With well-designed diene compounds 4, 23, and 24, RCM was found to be applicable to the formation of a highly strained skeleton of ingenol, and formal total synthesis of optically active ingenol (1) was achieved. The key features of this synthesis are construction of an A-ring by spirocyclization of ketone 21 with an allylic chloride unit and ring closure of a B-ring by olefin metathesis. Starting from Funk's keto ester 17, the key intermediate aldehyde 27 in Winkler's total synthesis was synthesized in eight steps in 12.5% overall yield. This strategy of direct cyclization of a strained inside-outside skeleton provided the first easy access to optically active ingenol.

DOI： 10.24496/tennenyuki.46.0_569

58(P-35) 海洋産抗腫瘍性物質アプリロニンA関連化合物の合成と生物活性(ポスター発表の部)

末永聖武, 黒田武史, 半田知久, 宮沙織, 兼松憲吾, 坂倉彰, 山田靜之, 木越英夫, 平田邦生, 高田昌樹, 加藤健一, 村岡真, 山本雅貴, 田中宏志

天然有機化合物討論会講演要旨集 ( 46 ) 323 - 328 2004年10月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Aplyronine A (1) is a potent antitumor macrolide isolated from the sea hare Aplysia kurodai, and mycalolide B (2) is a cytotoxic and antifungal macrolide isolated from a sponge of the genus Mycale. These macrolides interact with actin, one of the major proteins in cytoskeleton. We achieved total synthesis of aplyronine A (1) and its analogs and investigated the structure-activity relationships. We improved the synthesis of the side chain portion of aplyronine A (1) by using the Paterson aldol reaction and subsequent stereoselective reduction with Me_4NBH(OAc)_3 as key steps. The synthetic analogs 3 and 4 that only consists of the side chain part of aplyronine A (1) and mycalolide B (2) turned out to exhibit a strong actin depolymerizing activity, considering the size of the molecule. This result revealed that the side chain portion in aplyronine A (1) and mycalolide B (2) was responsible for the potent activity of 1 and 2. Analysis of the interaction of aplyronine analogs, such as 30 and 31, with actin by a photoaffinity labeling method has been carried out. Crystallization and X-ray structure analysis of actin complex with aplyronine A (1) also are in progress.

DOI： 10.24496/tennenyuki.46.0_323

Jolkinolide D pharmacophore: Synthesis and reaction with biomolecules 査読

Akira Sakakura, Yui Takayanagi, Hiroki Shimogawa, Hideo Kigoshi

Tetrahedron 60 ( 33 ) 7067 - 7075 2004年8月

Synthesis and actin-depolymerizing activity of mycalolide analogs 査読

Kiyotake Suenaga, Saori Miya, Takeshi Kuroda, Tomohisa Handa, Kengo Kanematsu, Akira Sakakura, Hideo Kigoshi

Tetrahedron Letters 45 ( 28 ) 5383 - 5386 2004年7月

Nonspecificity Induces Chiral Specificity in the Folding Transition of Giant DNA 査読

Michiko Ito, Akira Sakakura, Naomi Miyazawa, Shizuaki Murata, Kenichi Yoshikawa

Journal of the American Chemical Society 125 ( 42 ) 12714 - 12715 2003年10月

106(P-60) ジョルキノライドDファーマコホア : 合成とアミノ酸、ヌクレオシドおよびDNAに対する反応性(ポスター発表の部)

坂倉彰, 高柳維, 下川浩輝, 木越英夫

天然有機化合物討論会講演要旨集 ( 44 ) 623 - 628 2002年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Jolkinolide D (1) is a diterpenoid isolated from Euphorbia jolkini Boiss in 1974, and its stereostructure was recently determined by X-ray crystallographic analysis. It inhibited tumor invasion into the basement membrane and induced apoptosis in tumor cells. Jolkinolide D (1) has a γ,δ-unsaturated-β-hydroxy-α-methylene lactone unit as the pharmacophore structure, which suggests that jolkinolide D (1) might alkylate biomolecules such as proteins and DNA irreversibly. Since there are no other compounds that have the pharmacophore, reactivities of the unit toward nucleophiles have not hitherto been investigated. For the purpose of obtaining preliminary information on the chemical modification of biomolecules with jolkinolide D (1), jolkinolide D pharmacophore (2) was synthesized from 6-(tert-butyldimethylsilyloxy)-3-methyl-2-cyclohexenone (3) and 2-iodoallylalcohol (4), and its reactivity toward amino acids, nucleosides, and DNA was investigated. It was found that the order of reactivity of jolkinolide D pharmacophore (2) toward the nucleophiles in the amino acids at pH 7.5 is the thiol group in L-cysteine and glutathione > the imidazolyl group in L-histidine, the α-amino groups in amino acids > the carboxyl groups in amino acids. Jolkinolide D pharmacophore (2) alkylated 2'-deoxyguanosine at the N-1 position (pH 7.5) and thymidine at the N-3 position (pH 8.7), and modified DNA at the same sites in lower yields.

DOI： 10.24496/tennenyuki.44.0_623

Jolkinolide D pharmacophore: Synthesis and reaction with amino acids, nucleosides, and DNA 査読

Akira Sakakura, Yui Takayanagi, Hideo Kigoshi

Tetrahedron Letters 43 ( 34 ) 6055 - 6058 2002年8月

Effect of molecular sieves in the liquid-phase synthesis of nucleotides via the phosphoramidite method 査読

Yoshihiro Hayakawa, Akiyoshi Hirata, Jun-Ichiro Sugimoto, Rie Kawai, Akira Sakakura, Masanori Kataoka

Tetrahedron 57 ( 42 ) 8823 - 8826 2001年10月

A facile synthesis of 5′-end solid-anchored, 3′-end free oligodeoxyribonucleotides via the (5′→3′)-elongated phosphoramidite strategy 査読

Akira Sakakura, Yoshihiro Hayakawa

Nucleosides, Nucleotides and Nucleic Acids 20 ( 3 ) 213 - 227 2001年

Acid/azole complexes as highly effective promoters in the synthesis of DNA and RNA oligomers via the phosphoramidite method 査読

Y. Hayakawa, R. Kawai, A. Hirata, J. I. Sugimoto, M. Kataoka, A. Sakakura, M. Hirose, R. Noyori

Journal of the American Chemical Society 123 ( 34 ) 8165 - 8176 2001年

A novel synthesis of oligonucleotide-peptide conjugates with a base- labile phosphate linker between the two components according to the allyl- protected phosphoramidite strategy 査読

Akira Sakakura, Yoshihiro Hayakawa

Tetrahedron 56 ( 26 ) 4427 - 4435 2000年6月

An efficient synthesis of nucleotides via the phosphoramidite method using a triflic acid salt of an imidazole-related compound as a promoter.

A. Sakakura, M. Kataoka, R. Kawai, Y. Hayakawa

Nucleic acids symposium series ( 44 ) 137 - 138 2000年

A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates 査読

Akira Sakakura, Yoshihiro Hayakawa, Hitoshi Harada, Masaaki Hirose, Ryoji Noyori

Tetrahedron Letters 40 ( 23 ) 4359 - 4362 1999年6月

Aplyronine A, a potent antitumor substance of marine origin, aplyronines B and C, and artificial analogues: Total synthesis and structure-cytotoxicity relationships 査読

Hideo Kigoshi, Kiyotake Suenaga, Tsuyoshi Mutou, Takeshi Ishigaki, Toshiyuki Atsumi, Hiroyuki Ishiwata, Akira Sakakura, Takeshi Ogawa, Makoto Ojika, Kiyoyuki Yamada

Journal of Organic Chemistry 61 ( 16 ) 5326 - 5351 1996年8月

Absolute stereochemistry and synthesis of aplyronines B and C, the congeners of aplyronine A, a potent antitumor substance of marine origin 査読

Kiyotake Suenaga, Takeshi Ishigaki, Akira Sakakura, Hideo Kigoshi, Kiyoyuki Yamada

Tetrahedron Letters 36 ( 28 ) 5053 - 5056 1995年7月

Total synthesis of aplyronine A, a potent antitumor substance of marine origin 査読

Kigoshi Hideo, Ojika Makoto, Ishigaki Takeshi, Suenaga Kiyotake, Mutou Tsuyoshi, Sakakura Akira, Ogawa Takeshi, Yamada Kiyoyuki

Journal of the American Chemical Society 116 ( 16 ) 7443 - 7444 1994年8月

Synthetic Studies on Aplyronine A, a Potent Antitumor Substance of Marine Origin: Stereocontrolled Synthesis of the C21-C34 Segment 査読

Hideo Kigoshi, Makoto Ojika, Kiyotake Suenaga, Tsuyoshi Mutou, Junko Hirano, Akira Sakakura, Takeshi Ogawa, Masanori Nisiwaki, Kiyoyuki Yamada

Tetrahedron Letters 35 ( 8 ) 1247 - 1250 1994年2月

23 海産抗腫瘍性マクロリド、アプリロニンAの立体化学と合成研究(口頭発表の部)

木越英夫, 小鹿一, 石垣剛, 末永聖武, 武藤毅, 坂倉彰, 小川武, 西脇正憲, 塚田格, 山田靜之

天然有機化合物討論会講演要旨集 ( 35 ) 174 - 178 1993年9月

記述言語：日本語出版者・発行元：天然有機化合物討論会

Aplyronine A (1) is a potent antitumor macrolide isolated as a minute component from the sea hare Aplysia kurodai. The gross structure of 1 was determined by the spectral analysis and chemical degradation. We report herein the absolute stereostructure of 1 and the result of the synthetic study. Chemical degradation of 1 afforded five fragments 2-6. Enantioselective syntheses of the fragments 4a and 5a were performed to disclose the absolute stereochemistry of seven chiral centers (C7-C10, C13, C17, and C19). HPLC analyses of the fragments 2 and 3 using chiral columns disclosed that N,N,O-trimethylserine and N,N-dimethylalanine moieties of 1 were scalemic mixtures (S:R=52:48 for 2; 72:28 for 3). On the basis of the result of the previous and present studies, the absolute stereostructure of aplyronine A (1) was elucidated unambiguously. The synthetic study of 1 was carried out using the Evans aldol reaction and the Sharpless epoxidation reaction as key steps. Starting from N-propionylurethane 11, the C5-C20 segment 13 and the C21-C34 segment 16 were synthesized. The Julia coupling reaction of 13 with 16 followed by four-carbons homologation and lactonization provided 24-membered lactone 17.

DOI： 10.24496/tennenyuki.35.0_174