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

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)4418-4421
Number of pages4
JournalOrganic Letters
Volume14
Issue number17
DOIs
Publication statusPublished - 2012 Sep 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kimura, T., Kanagaki, S., Matsui, Y., Imoto, M., Watanabe, T., & Shibasaki, M. (2012). Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017. Organic Letters, 14(17), 4418-4421. https://doi.org/10.1021/ol3019314