A general procedure for the synthesis of stereochemically pure conduritol derivatives practical also for solid-phase chemistry

A straightforward synthetic protocol apt to synthesize a library constituted by all conduritol stereoisomers in solution phase is described and successfully applied to some polymer-supported substrates. During the solid-phase sequence, an unprecedented rearrangement of a resin-bound sulfone performed under the Ramberg-Backlund conditions appears of particular interest. Upon treatment with Me3Si-I, thiepanes supported on resin are found to undergo regio- and stereospecific ring contraction to a six-membered ring system with traceless cleavage from the solid support.