論文 - 坂倉　彰

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

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記述言語：英語  

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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

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

The C21-C34 segment 2 of aplyronine A (1), a potent antitumor substance of marine origin, was synthesized enantioselectively in 25 steps (17% overall yield) from imide 11. © 1994.

DOI： 10.1016/0040-4039(94)88035-2

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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

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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

CiNii Article

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