Total Synthesis of Basiliskamides A and B

Darren J. Lipomi, Neil F. Langille, and James S. Panek*
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts, 02215
Org. Lett., 2004, 6 (20), pp 3533–3536
DOI: 10.1021/ol048574m
Publication Date (Web): September 1, 2004
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7−C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

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    History

    • Published In Issue September 30, 2004
    • Received July 22, 2004

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