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. 2008 Oct 2;10(19):4315-8.
doi: 10.1021/ol801760w. Epub 2008 Aug 30.

Au(I)-catalyzed ring expanding cycloisomerizations: total synthesis of ventricosene

Steven G Sethofer  1 , Steven T Staben, Olivia Y Hung, F Dean Toste
Affiliations

Au(I)-catalyzed ring expanding cycloisomerizations: total synthesis of ventricosene

Steven G Sethofer et al. Org Lett. .

Abstract

The gold(I)-catalyzed cycloisomerization of enynes containing an embedded cyclopropane unit leads selectively to the formation of ring systems containing the cyclopropylmethyl cation. A subsequent Wagner-Merwein shift provides diastereomerically pure fused cyclobutanes. The utility of this methodology for the rapid assembly of polycyclic ring systems is illustrated by the total synthesis of the angular triquinane ventricosene.

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Figures

Scheme 1
Scheme 1
Cycloisomerization of Alkylidenecyclopropanes
Scheme 2
Scheme 2
Stereochemical Analysis of Cyclopropanol Cycloisomerization
Scheme 3
Scheme 3
Synthesis of Ventricos-7(13)-ene 22
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