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

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• 作者：Tomoyuki Kimura ; Shuhei Kanagaki ; Yusuke Matsui ; Masaya Imoto ; Takumi Watanabe ; Masakatsu Shibasaki
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 7, 2012
• 年：2012
• 卷：14
• 期：17
• 页码：4418-4421
• 全文大小：278K
• 年卷期：v.14,no.17(September 7, 2012)
• ISSN：1523-7052

文摘

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).