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

doi:10.1021/ja2047232

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

108 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 language	English
Pages (from-to)	14710-14726
Number of pages	17
Journal	Journal of the American Chemical Society
Volume	133
Issue number	37
DOIs	https://doi.org/10.1021/ja2047232
Publication status	Published - 2011 Sep 21
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja2047232

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title = "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.",

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AU - Seiple, Ian B.

AU - Su, Shun

AU - Young, Ian S.

AU - Nakamura, Akifumi

AU - Yamaguchi, Junichiro

AU - Jørgensen, Lars

AU - Rodriguez, Rodrigo A.

AU - Ömalley, Daniel P.

AU - Gaich, Tanja

AU - Köck, Matthias

AU - Baran, Phil S.

PY - 2011/9/21

Y1 - 2011/9/21

N2 - 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.

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

Abstract

ASJC Scopus subject areas

UN SDGs

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