Preparation and Transformations of Three p-Menthane-3-methanesulfonyloxy-4,8-diols

Abstract

Three diastereomeric p-menthane-3-methanesulfonyloxy-4,8-diols were synthesized from (+)-pulegone. Treatment of each methanesulfonate with aqueous base resulted in a stereospecific reaction involving antiperiplanar groups to give one product: either an α-ketol by a pinacol-type rearrangement or an epoxide by an intramolecular SN2-type reaction. Although the possibility existed for 1,3- as well as 1,2-diol monomethanesulfonate transformations, only products from the latter type of reaction were isolated.