Synthesis of (+)-Elaeokanine A and (+)-Elaeokanine C Based upon a Novel Approach Involving Diastereoselective, Nucleophilic Addition to N-Acyliminium Ion and Retro Diels-Alder Reaction

Article abstract of DOI:10.1016/S0957-4166(00)80260-8

An asymmetric synthesis of Elaeocarpus alkaloids, (+)-elaeokanine A and (+)-elaeokanine C is described.The key steps involve an asymmetric Diels-Alder reaction of a chiral sulfinyl dienophile, diastereoselective nucleophilic addition to the acyliminium ion and retro Diels-Alder reactions.