Stereoselective Reactions of a (−)-Quinic Acid-Derived Enone:  Application to the Synthesis of the Core of Scyphostatin

Abstract

[reaction: see text] A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.