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

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journal contribution
posted on 26.01.1996, 00:00 by Anthony G. M. Barrett, Mark L. Boys, Terri L. Boehm
The total synthesis of (+)-papuamine, the antipode of the C2-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.

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