A General Procedure for the Synthesis of Stereochemically Pure Conduritol Derivatives Practical also for Solid-Phase Chemistry

摘要

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- Backhand conditions appears of particular interest.Upon treatment with Me_3Si- 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.