A ring closing metathesis strategy for carbapyranosides of xylose and arabinose

Abstract

The synthesis of β-carba-xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether–alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration–oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.