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Polyketide assembly by alkene-alkyne reductive cross-coupling: Spiroketals through the union of homoallylic alcohols

Academic Article
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Overview

authors

  • Canterbury, D. P.
  • Micalizio, Glenn

publication date

  • June 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A reaction sequence composed of regioselective formal hydroalkynylation, reductive ene-yne cross-coupling, and oxidative cyclization has been developed to prepare stereochemically dense spiroketals. Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene.

subject areas

  • Alcohols
  • Alkenes
  • Alkynes
  • Cyclization
  • Furans
  • Oxidation-Reduction
  • Spiro Compounds
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2892691

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja102888f

PubMed ID

  • 20476790
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Additional Document Info

start page

  • 7602

end page

  • 7604

volume

  • 132

issue

  • 22

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