Enantioselective total synthesis of (-)-chlorothricolide via the tandem inter- and intramolecular Diels-Alder reaction of a hexaenoate intermediate

An enantioselective total synthesis of (-)-chlorothricolide was completed through the tandem inter- and intramolecular Diels-Alder reaction of a hexaenoate intermediate. The synthesis proceeds in approximately 2% overall yield and 20 steps using the longest linear sequence originating from the known acetylemic ketone. Results indicate that the Diels-Alder reaction method is feasible only by virtue of the exceptionally high diastereofacial and exo selectivity of the chiral dienophile.