4.8 Article

An Enantioselective Total Synthesis and Stereochennical Revision of (+)-Citrinadin B

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 30, Pages 10890-10893

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja405548b

Keywords

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Funding

  1. Amgen
  2. Bristol-Myers Squibb
  3. NSF [CHE-1058292]
  4. NIH [GM095076]
  5. Kitasato Institute
  6. Uehara Foundation
  7. Division Of Chemistry
  8. Direct For Mathematical & Physical Scien [1058292] Funding Source: National Science Foundation

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This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

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