4.4 Article

Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization

Journal

TETRAHEDRON
Volume 65, Issue 26, Pages 4957-4967

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.03.103

Keywords

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Funding

  1. NIH [GM-079339]
  2. Boehringer-Ingelheim
  3. Bristol Myers Squibb
  4. Eli Lilly
  5. Packard Foundation
  6. Beckman Foundation
  7. Sloan Foundation

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An N-heterocyclic carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic gamma-lactam-gamma-lactone adducts from enals is reported. This method has been applied to the formal synthesis of salinosporamide A, a potent 20S proteasome inhibitor and anti-cancer therapeutic. (C) 2009 Elsevier Ltd. All rights reserved.

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