Asymmetric synthesis of (+)-(S)-Massoia lactone, pheromone of Idea leuconoe. Formal total synthesis of valilactone and lachnelluloic acid

Abstract

Simple and efficient asymmetric synthesis was developed of the cyclic scaffold of (-)-valilactone, an effective inhibitor of the pancreas lipase, applying the Keck allylation in the key stage of building up the carbon skeleton of the target molecule and of the unnatural (S)-isomer of Massoia lactone, lachnelluloic acid, possessing fungicidal properties, and (5R,7S)-7-hydroxy-5-dodecanolid, pheromone component of the Large Tree Nymph butterfly Idea leuconoe.