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

Department of Biosciences and Informatics

Research output: Contribution to journal › Article › peer-review

28 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 language	English
Pages (from-to)	4418-4421
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol3019314
Publication status	Published - 2012 Sep 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3019314

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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).",

author = "Tomoyuki Kimura and Shuhei Kanagaki and Yusuke Matsui and Masaya Imoto and Takumi Watanabe and Masakatsu Shibasaki",

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AU - Kimura, Tomoyuki

AU - Kanagaki, Shuhei

AU - Matsui, Yusuke

AU - Imoto, Masaya

AU - Watanabe, Takumi

AU - Shibasaki, Masakatsu

PY - 2012/9/7

Y1 - 2012/9/7

N2 - 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).

AB - 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).

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

Abstract

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