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

23 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

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alkaloids
stereochemistry
Alkaloids
Stereochemistry
osmium
apoptosis
synthesis
configurations
Optical rotation
Vacuolar Proton-Translocating ATPases
Osmium
Optical Rotation
Epidermal Growth Factor Receptor
Epidermal Growth Factor
profiles
cells
High Pressure Liquid Chromatography
Apoptosis
molecules
Molecules

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017. / Kimura, Tomoyuki; Kanagaki, Shuhei; Matsui, Yusuke; Imoto, Masaya; Watanabe, Takumi; Shibasaki, Masakatsu.

In: Organic Letters, Vol. 14, No. 17, 07.09.2012, p. 4418-4421.

Research output: Contribution to journalArticle

Kimura, Tomoyuki ; Kanagaki, Shuhei ; Matsui, Yusuke ; Imoto, Masaya ; Watanabe, Takumi ; Shibasaki, Masakatsu. / Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017. In: Organic Letters. 2012 ; Vol. 14, No. 17. pp. 4418-4421.
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