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Total synthesis of (-)-spinosyn A

Academic Article
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Overview

authors

  • Mergott, D. J.
  • Frank, S. A.
  • Roush, William

publication date

  • August 2004

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • A convergent, highly stereoselective total synthesis of (-)-spinosyn A (1) is described. Key features of the synthesis include the transannular Diels-Alder reaction of macrocyclic pentaene 11 and the transannular Morita-Baylis-Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (-)-spinosyn A was completed by a sequence involving the highly beta-selective glycosidation reaction of 13 and glycosyl imidate 30.

subject areas

  • Chemistry, Organic
  • Insecticides
  • Macrolides
  • Molecular Structure
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC514415

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.0401247101

PubMed ID

  • 15173590
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Additional Document Info

start page

  • 11955

end page

  • 11959

volume

  • 101

issue

  • 33

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