Synthesis of the (4S, 5R)-5-hydroxy-decan-4-olide (L-factor) and of the (R)-decan-4-olide from a chiral sulphoxide

The condensation of optically pure (+)-R-n-hexyl 4-methylphenyl sulphoxide () on the succinic diester () produced the 4-oxo-5-sulphinyl decanoate which was selectively reduced to the corresponding 4-hydroxy-5-sulphinyl decanoates . Starting from the (4S, 5S, RS) pure alcohol , a five-step sequence produced the (4S, 5R)-5-hydroxy-decan-4-olide () (L-Factor) and a three-step sequence gave the (R)-decan-4-olide (). In both cases final natural products were obtained in good overall yields and in optical pure form.