Asymmetric synthesis of 5-hexadecanolide, pheromone of the queen of the Oriental hornet, Vespa orientalis

Article abstract of DOI:10.1016/0040-4020(96)00095-6

An efficient asymmetric synthesis of 5-hexadecanolide from a chiral epoxide is described. Both the enantiomeric forms of the chiral epoxide are easily available from mannitol and ascorbic acid. The key step in the synthesis is the formation of δ-lactone from δ-hydroxy acetal using m-CPBA and BF₃-OEt₂.