Synthesis and Assignment of the Absolute Configuration of Indenotryptoline Bisindole Alkaloid BE-54017

被引：32

作者：

Kimura, Tomoyuki ^{[1
]}

Kanagaki, Shuhei ^{[2
]}

Matsui, Yusuke ^{[2
]}

Imoto, Masaya ^{[2
]}

Watanabe, Takumi ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

[2] Keio Univ, Dept Biosci & Informat, Fac Sci & Technol, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

关键词：

ISOGRANULATIMIDE ANALOGS; BIOLOGICAL-ACTIVITY; INHIBITORS; DIHYDROXYLATION; STAUROSPORINE; BIOSYNTHESIS; REBECCAMYCIN; PRODUCTS; OLEFINS;

D O I：

10.1021/ol3019314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 otation 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).

引用

页码：4418 / 4421

页数：4

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