Title

A Concise, Biomimetic Total Synthesis of (+)-Davanone

Student Co-author

Pomona Undergraduate, HMC Undergraduate

Document Type

Article

Department

Chemistry (HMC), Mathematics (Pomona)

Publication Date

2009

Abstract

A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.

Rights Information

© 2009 American Chemical Society