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

doi:10.1021/ol3019314

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

生命情報学科

研究成果: Article › 査読

26 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
巻	14
号	17
DOI	https://doi.org/10.1021/ol3019314
出版ステータス	Published - 2012 9 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3019314

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引用スタイル

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AU - Watanabe, Takumi

AU - Shibasaki, Masakatsu

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