Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017

Tomoyuki Kimura, Shuhei Kanagaki, Yusuke Matsui, Masaya Imoto, Takumi Watanabe, Masakatsu Shibasaki

研究成果: Article査読

29 被引用数 (Scopus)

抄録

Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).

本文言語English
ページ(範囲)4418-4421
ページ数4
ジャーナルOrganic Letters
14
17
DOI
出版ステータスPublished - 2012 9 7

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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