4.4 Article

Carbocation rearrangements in aspernomine biosynthesis

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 14, Pages 1578-1581

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.01.098

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Funding

  1. American Chemical Society Petroleum Research Fund
  2. University of California, Davis
  3. National Science Foundation CAREER
  4. National Science Foundation's

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Quantum chemical calculations (B3LYP/6-31G(d)) on carbocation rearrangements that are proposed to occur in the biosynthesis of aspernomine are described. Based on these calculations, a pathway involving a concerted but asynchronous [4+2] cycloaddition that avoids the formation of a secondary carbocation is proposed for small model systems. (C) 2009 Elsevier Ltd. All rights reserved.

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