Ring Expansions of β-Keto Lactones with Zinc Carbenoids: Syntheses of (+)-Patulolide A and (±)-Patulolide B
- 30 January 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (5) , 1878-1885
- https://doi.org/10.1021/jo0264776
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.Keywords
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