Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol

A novel approach to natural β-hydroxy-γ-lactone from 2,5-anhydro-d-mannitol () is described. The key reactions in this synthesis include stereoselective methylation of aldehyde with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate and an intermolecular cross-metathesis of 3-allyl-4-hydroxy-γ-lactone with 1-tridecene.