Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene

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 methodolo...

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Veröffentlicht in:Organic letters 2008-10, Vol.10 (19), p.4315-4318
Hauptverfasser: Sethofer, Steven G, Staben, Steven T, Hung, Olivia Y, Toste, F. Dean
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801760w