Stereoselective synthesis of either (±)-exo- or (±)-endo-brevicomin via hydride reduction of a 2-acylpyranyl intermediate
Abstract
Reduction of the ethyl ketone (5) with L-Selectride or zinc borohydride proceeds stereoselectively to give the alcohols syn-(6) or anti-(7), respectively, which are converted, in turn, into (±)-exo-brevicomin and (±)-endo-brevicomin.