title: Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp.
abstract: 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.
authors.affiliation: Departments of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England, and Colorado State University, Fort Collins Colorado 80523.
authors.forename: Anthony G. M.
authors.initials: AG
authors.lastname: Barrett
authors.forename: Mark L.
authors.initials: ML
authors.lastname: Boys
authors.forename: Terri L.
authors.initials: TL
authors.lastname: Boehm