Total Synthesis of (-)-Decarestrictine J

Abstract

The synthesis of (-)-decarestrictine J (1), a novel inhibitor of the cholesterol biosynthesis, is described. (-)-Epoxy alcohol 6, which was obtained by the Sharpless asymmetric epoxidation of trans-allylic alcohol 13, was converted to bromoacetoxy aldehyde 3 through a nine-step sequence. The samarium(II)iodide-promoted intramolecular Reformatsky reaction of 3 and subsequent oxidation afforded keto lactone 21 which, by treating with trimethylsilyl bromide, provided (-)-decarestrictine J (1).