Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp.
The total synthesis of (+)-papuamine, the antipode of the C(2)-symmetric, optically active, pentacyclic diamine natural product, starting from a chiral diol is described. The diol is available via an asymmetric Diels-Alder reaction between 1,3-butadiene and di-(-)-menthyl fumarate. The key transformation in the synthesis is an intramolecular Pd(0)-catalyzed (Stille) coupling reaction to form the central 13-membered diazadiene macrocyclic ring.
Barrett
Anthony G. M.
AG
Departments of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England, and Colorado State University, Fort Collins Colorado 80523.
Boys
Mark L.
ML
Boehm
Terri L.
TL