Syntheses and Biological Evaluation of Irciniastatin A and the C1−C2 Alkyne Analogue

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• 作者：Tsubasa Watanabe ; Takamichi Imaizumi ; Takumi Chinen ; Yoko Nagumo ; Masatoshi Shibuya ; Takeo Usui ; Naoki Kanoh ; Yoshiharu Iwabuchi
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：March 5, 2010
• 年：2010
• 卷：12
• 期：5
• 页码：1040-1043
• 全文大小：272K
• 年卷期：v.12,no.5(March 5, 2010)
• ISSN：1523-7052

文摘

Syntheses of both natural (+)- and unnatural (−)-irciniastatin A (aka psymberin) as well as a C1−C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1−C6, C8−C16, and C17−C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (−)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.