4.8 Article

Concise Total Synthesis and Stereochemical Revision of all (-)-Trigonoliimines

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 28, Pages 10768-10771

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja204597k

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Funding

  1. NIH-NIGMS [GM074825]
  2. NSF [CHE-0946721]
  3. Amgen
  4. DuPont

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The concise and enantioselective total syntheses of (-)-trigonoliimines A, B, and C are described. Our unified strategy to all three natural products is based on asymmetric oxidation and reorganization of a single bistryptamine, a sequence of transformations with possible biogenetic relevance. We revise the absolute stereo chemistry of (-)-trigonoliimines A, B, and C.

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