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

Ian B. Seiple, Shun Su, Ian S. Young, Akifumi Nakamura, Junichiro Yamaguchi, Lars Jørgensen, Rodrigo A. Rodriguez, Daniel P. Ömalley, Tanja Gaich, Matthias Köck, Phil S. Baran

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89 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)14710-14726
Number of pages17
JournalJournal of the American Chemical Society
Volume133
Issue number37
DOIs
Publication statusPublished - 2011 Sep 21
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Seiple, I. B., Su, S., Young, I. S., Nakamura, A., Yamaguchi, J., Jørgensen, L., Rodriguez, R. A., Ömalley, D. P., Gaich, T., Köck, M., & Baran, P. S. (2011). Enantioselective total syntheses of (-)-palau'Amine, (-)-axinellamines, and (-)-massadines. Journal of the American Chemical Society, 133(37), 14710-14726. https://doi.org/10.1021/ja2047232