RCM/PCC oxidation strategy for synthesis of functionalized cyclic alpha,beta-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

Abstract

A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006