Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide

  • J Org Chem. 2006 Sep 29;71(20):7866-9. doi: 10.1021/jo061278y.
Gonzalo Blay  1 ,  Begoña García ,  Eva Molina ,  José R Pedro
Affiliations
  • 1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100, Burjassot, València, Spain.
PMID: 16995700 DOI: 10.1021/jo061278y
Abstract

The first total syntheses of (+)-alismoxide and (+)-4-epi-alismoxide are reported. Formal chemo-, regio-, and stereoselective addition of water to 10alpha-acetoxy-1alphaH,5betaH-guaia-3,6-diene afforded the target compounds after reduction. The absolute stereochemistry of (+)-alismoxide has been established. The low [alpha](D) +8.6 value indicates that significant amounts of alismoxide result from biosynthetic processes. Furthermore, the structure of the natural guaienediol isolated from Silphium perfoliatum has been corrected to (-)-alismoxide.

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