Efficient Synthesis of (-)-Osmundalactone and Its Epimer from Carbohydrate Precursor

Abstract

An efficient total synthesis of α,β-unsaturated 6-membered lactones, (-)-osmundalactone and its epimer (6epi-(+)-osmundalactone) has been achieved from carbohydrates derivatives, L-arabinose and D-xylose, employing hydrolysis of diol, Horner-Wittig reaction and formate ester hydrolysis followed by δ-lactonization in acidic medium as key steps. The overall yields of (-)-osmundalactone and its epimer is significantly more.