Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.

Journal of the American Chemical Society
Xinpei CaiMingji Dai

Abstract

A novel palladium-catalyzed ring opening carbonylative lactonization of readily available hydroxycyclopropanols was developed to efficiently synthesize tetrahydrofuran (THF) or tetrahydropyran (THP)-fused bicyclic γ-lactones, two privileged scaffolds often found in natural products. The reaction features mild reaction conditions, good functional group tolerability, and scalability. Its application was demonstrated in a short total synthesis of (±)-paeonilide. The fused bicyclic γ-lactone products can be easily diversified to other medicinally important scaffolds, which further broadens the application of this new carbonylation method.

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Citations

Mar 31, 2021·Angewandte Chemie·Zhao YangMin Zhang
Aug 4, 2021·The Journal of Organic Chemistry·Lipeng LongZhengwang Chen
Oct 30, 2021·Journal of the American Chemical Society·Yoshiya Sekiguchi, Naohiko Yoshikai

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