Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.