Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol

Abstract

γ-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol.