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Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

ABSTRACT: Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels-Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments, are described.

SUBMITTER: Seiple IB 

PROVIDER: S-EPMC3173569 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Seiple Ian B IB   Su Shun S   Young Ian S IS   Nakamura Akifumi A   Yamaguchi Junichiro J   Jørgensen Lars L   Rodriguez Rodrigo A RA   O'Malley Daniel P DP   Gaich Tanja T   Köck Matthias M   Baran Phil S PS  

Journal of the American Chemical Society 20110823 37

Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. N  ...[more]

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