Total synthesis of basiliskamides A and B

Organic Letters
Darren J LipomiJames S Panek

Abstract

[structure: see text] 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).

References

Aug 31, 2002·Organic Letters·Yumika OkadaNobuhiro Fusetani

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Citations

Mar 1, 2012·Organic Letters·Ming Chen, William R Roush
Feb 3, 2006·Natural Product Reports·Gillian M Nicholas, Andrew J Phillips
Feb 3, 2006·Natural Product Reports·John W BluntMichèle R Prinsep
Dec 10, 2015·Journal of the American Chemical Society·Taku KitanosonoShu̅ Kobayashi
Sep 25, 2017·Nature Chemistry·Michael A CorselloNeil K Garg
Dec 6, 2018·Accounts of Chemical Research·Andrew T Kleinschmidt, Darren J Lipomi

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