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Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

ABSTRACT: A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

SUBMITTER: Kieffer ME

PROVIDER: S-EPMC3662218 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Kieffer Madeleine E ME Chuang Kangway V KV Reisman Sarah E SE

Journal of the American Chemical Society 20130403 15

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B. ...[more]

PMID: 23540731

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