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A concise, biomimetic total synthesis of (+)-davanone
Karen C Morrison1, Jonathan P Litz, Kathryn P Scherpelz
1Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, USA.
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.
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