Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

Tsubasa Watanabe, Takamichi Imaizumi, Takumi Chinen, Yoko Nagumo, Masatoshi Shibuya, Takeo Usui, Naoki Kanoh, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

"Chemical equation presented" 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.

Original languageEnglish
Pages (from-to)1040-1043
Number of pages4
JournalOrganic letters
Volume12
Issue number5
DOIs
Publication statusPublished - 2010 Mar 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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