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

Version 1

      Publication Details (including relevant citation   information):

      Morrison,   K.C.;   Litz, J.P.; Scherpelz, K.P.; Dossa, P.D.; Vosburg, D.A. “A   Concise, Biomimetic Total Synthesis of (+)-Davanone” Org.   Lett. 2009, 11, 2217-2218.


      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.

      Address (URL): http://dx.doi.org/10.1021/ol900697w