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. 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

Hee Nam Lim  1 , Kathlyn A Parker
Affiliations

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

Hee Nam Lim et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1
Nonenzymatic 8π, 6π Electrocyclization of E, Z, Z, Z Tetraene 4
Scheme 2
Scheme 2
The Postulated Key Step for the Total Synthesis, Tandem Coupling and [1,7]-Hydrogen Shift
Scheme 3
Scheme 3
Tandem Reaction in Model System
Scheme 4
Scheme 4
Synthesis of the Iododiene 6
Scheme 5
Scheme 5
Convergent Synthesis of (−)-Arabilin
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