Ring Expansions of β-Keto Lactones with Zinc Carbenoids: Synthesis of (+)-Patulolide A

Abstract

A one-pot ring expansion/oxidation/elimination method has been developed in which β-keto lactones are converted efficiently to α,β-unsaturated-γ-keto lactones. The reaction can be successfully applied to a variety of ring sizes. Alkene stereochemistry is dependent upon ring size and reaction conditions. The method was applied to the synthesis of (+)-patulolide A.

Department

Chemistry

Publication Date

3-1-2003

Journal Title

Journal of Organic Chemistry

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/jo0264776

Document Type

Article

Rights

Copyright © 2003, American Chemical Society

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