100207-79-2Relevant articles and documents
Construction of the Taxane C-Ring Epoxy Alcohol Moiety and Examination of Its Possible Involvement in the Biogenesis of the Taxane 3-Oxetanol Structure
Swindell, Charles S.,Britcher, Susan F.
, p. 793 - 797 (2007/10/02)
A stereospecific synthesis of a model compound containing the 2,3-epoxy alcohol moiety present in the C ring of several taxane diterpenes has been devised.Thus epoxide 8 was converted to allylic alcohol 9 which upon epoxidation to give 10 followed by treatment with hydroxide afforded 11, the epoxy alcohol.Derived methanesulfonate 13 was found to yield 14 upon solvolysis in aqueous acetonitrile.Two possible mechanisms for this transformation are provided.This last experiment was designed to evaluate a described suggestion regarding the biogenesis of the taxane C-ring 3-oxetanol moiety.