Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017
Tomoyuki Kimura1, Shuhei Kanagaki, Yusuke Matsui
1Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Tokyo 141-0021, Japan.
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).
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