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J Am Chem Soc. 2011 Sep 21;133(37):14710-26. doi: 10.1021/ja2047232. Epub 2011 Aug 23.

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

Author information

1
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

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.

PMID:
21861522
PMCID:
PMC3173569
DOI:
10.1021/ja2047232
[Indexed for MEDLINE]
Free PMC Article

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