4.8 Article

Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 15, Pages 5557-5560

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja4023557

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Funding

  1. National Science Foundation [DGE-1144469]
  2. California Institute of Technology
  3. Amgen
  4. DuPont
  5. NIH [NIGMS RGM097582A]

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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.

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