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 | |
| Publication status | Published - 2012 Sep 7 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Kimura, T., Kanagaki, S., Matsui, Y., Imoto, M., Watanabe, T., & Shibasaki, M. (2012). Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017. Organic Letters, 14(17), 4418-4421. https://doi.org/10.1021/ol3019314