4.7 Article

Enantio- and diastereocontrolled total synthesis of (+)-boronolide

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 10, Pages 3935-3941

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo0603781

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An efficient stereoselective total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric hydroxylation, a chelation-controlled vinyl Grignard reaction followed by a Sharpless asymmetric epoxidation, hydrolytic kinetic resolution, and a ring-closing metathesis.

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