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Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

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2011

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Seiple, Ian B.
Su, Shun
Young, Ian S.
Nakamura, Akifumi
Yamaguchi, Junichiro
Jørgensen, Lars
Rodriguez, Rodrigo A.
O’Malley, Daniel P.
Köck, Matthias
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https://doi.org/10.1021/ja2047232
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Journal of the American Chemical Society. 2011, 133(37), pp. 14710-14726. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja2047232

Zusammenfassung

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.

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540 Chemie

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ISO 690SEIPLE, Ian B., Shun SU, Ian S. YOUNG, Akifumi NAKAMURA, Junichiro YAMAGUCHI, Lars JØRGENSEN, Rodrigo A. RODRIGUEZ, Daniel P. O’MALLEY, Tanja GAICH, Matthias KÖCK, Phil S. BARAN, 2011. Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines. In: Journal of the American Chemical Society. 2011, 133(37), pp. 14710-14726. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja2047232
BibTex
@article{Seiple2011-09-21Enant-38286,
  year={2011},
  doi={10.1021/ja2047232},
  title={Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines},
  number={37},
  volume={133},
  issn={0002-7863},
  journal={Journal of the American Chemical Society},
  pages={14710--14726},
  author={Seiple, Ian B. and Su, Shun and Young, Ian S. and Nakamura, Akifumi and Yamaguchi, Junichiro and Jørgensen, Lars and Rodriguez, Rodrigo A. and O’Malley, Daniel P. and Gaich, Tanja and Köck, Matthias and Baran, Phil S.}
}
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    <dcterms:abstract xml:lang="eng">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.</dcterms:abstract>
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