Enantiospecific synthesis of functionalized polyols from tartaric acid using Ley's dithiaketalization: Application to the total synthesis of achaetolide

Synthesis of chiral tetrols and 1,2,4-triols with varied substitutions was accomplished from tartaric acid. Pivotal reaction in the synthesis was the use of Ley's dithianylation of an alkynyl ketone derived from tartaric acid. Application of the strategy was demonstrated in the total synthesis of decanolactone achaetolide.