A Concise, Biomimetic Total Synthesis of (+)-Davanone
Chemistry (HMC), Mathematics (Pomona)
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.
© 2009 American Chemical Society
“A concise, biomimetic total synthesis of (+)-davanone,” Morrison, K.C.; Litz, J.P.; Scherpelz, K.P.; Dossa, P.D.; Vosburg, D.A. Org. Lett. 2009, 11, 2217-2218. DOI: 10.1021/ol900697w