Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp

Anthony G. M. Barrett; Mark L. Boys; Terri L. Boehm

doi:10.1021/jo951413z

Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp

J Org Chem. 1996 Jan 26;61(2):685-699. doi: 10.1021/jo951413z.

Authors

Anthony G. M. Barrett¹, Mark L. Boys, Terri L. Boehm

Affiliation

¹ Departments of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England, and Colorado State University, Fort Collins Colorado 80523.

PMID: 11666992
DOI: 10.1021/jo951413z

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.