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J Am Chem Soc. 2011 Dec 21;133(50):20149-51. doi: 10.1021/ja209459f. Epub 2011 Nov 29.

Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

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  • 1Department of Chemistry, Stony Brook University, Stony Brook, New York 11794, USA.

Erratum in

  • J Am Chem Soc. 2012 Mar 7;134(9):4449.

Abstract

The first total synthesis of (-)-arabilin, a Streptomyces metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic.

© 2011 American Chemical Society

PMID:
22085260
[PubMed - indexed for MEDLINE]
PMCID:
PMC3320024
Free PMC Article
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