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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Bibliographic Details
Published inOrganic letters Vol. 10; no. 19; pp. 4315 - 4318
Main Authors Sethofer, Steven G, Staben, Steven T, Hung, Olivia Y, Toste, F. Dean
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2008
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Gold - chemistry
Isomerism
Physical Sciences
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Science & Technology
Sesquiterpenes - chemical synthesis
REARRANGEMENT
CATALYZED CYCLOISOMERIZATION
ORGANIC-SYNTHESIS
GOLD CATALYSIS
REDUCING AGENT
CYCLOPROPANATION
CHEMISTRY
DERIVATIVES
CYCLIZATION
ENYNES
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol801760w