(+)-Pleuromutilin Synthetic Studies. Direct Degradation to and Independent Preparation of an Advanced Diketone Intermediate. Demonstration that Reconstruction of the Eight-Membered Ring Suffers from Serious Kinetic Retardation.

Article abstract of DOI:10.1021/jo00242a020

Levorotatory lactone 2 has been converted into (-)-bicyclic ketone 3, an intermediate containing all 20 carbon atoms of the pleuromutilin target.Pleuromutilin and tiamulin have in turn been degraded to this important relay compound in only four steps.Vari