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Studies on the synthesis of (-)-spinosyn A: application of the steric directing group strategy to transannular Diels-Alder reactions

Academic Article
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Overview

authors

  • Frank, S. A.
  • Roush, William

publication date

  • June 2002

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A highly diastereoselective and enantioselective synthesis of the decahydro-as-indacene nucleus 12 of (-)-spinosyn A (1) is reported. By implementing the steric directing group strategy, tricyclic lactone 37 was produced from a remarkably diastereoselective transannular Diels-Alder reaction of lactone 9. The tricyclic core of the natural product was then obtained by using an Ireland-Claisen ring contraction of 37. Reversal of the order of these two steps resulted in an almost complete loss of diastereoselectivity.

subject areas

  • Anti-Bacterial Agents
  • Catalysis
  • Chemistry, Organic
  • Cyclization
  • Heterocyclic Compounds
  • Macrolides
  • Molecular Structure
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo025580s

PubMed ID

  • 12054969
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Additional Document Info

start page

  • 4316

end page

  • 4324

volume

  • 67

issue

  • 12

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