Consecutive Alkene Cross-Metathesis/Oxonium Ylide Formation−Rearrangement: Synthesis of the Anti-HIV Agent Hyperolactone C

α-Diazo-β-ketoesters bearing allylic ether functionality undergo highly stereoselective Ru-carbene-catalyzed alkene cross-metathesis followed by Rh2(OAc)4-catalyzed oxonium ylide formation/[2,3] sigmatropic rearrangement in a one-flask operation and in a highly diastereoselective manner. The methodo...

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Bibliographic Details
Published in:Organic letters 2008-12, Vol.10 (24), p.5553-5556
Main Authors: Hodgson, David M, Angrish, Deepshikha, Erickson, Stephanie P, Kloesges, Johannes, Lee, Caroline H
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Anti-HIV Agents - chemical synthesis
Crystallography, X-Ray
Furans - chemical synthesis
Molecular Structure
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Summary:α-Diazo-β-ketoesters bearing allylic ether functionality undergo highly stereoselective Ru-carbene-catalyzed alkene cross-metathesis followed by Rh2(OAc)4-catalyzed oxonium ylide formation/[2,3] sigmatropic rearrangement in a one-flask operation and in a highly diastereoselective manner. The methodology has been demonstrated in a concise synthesis of the anti-HIV agent hyperolactone C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802334y