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[3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. Studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins

Academic Article
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Overview

authors

  • Mertz, E.
  • Tinsley, J. M.
  • Roush, William

publication date

  • September 2005

journal

  • Journal of Organic Chemistry  Journal

abstract

  • [Structure: See text] Double asymmetric [3 + 2]-annulation reactions of chiral beta-silyloxyallylsilanes with chiral 2-tetrahydrofuranyl carboxaldehydes have been studied, leading to the stereocontrolled synthesis of six diastereomeric bis-tetrahydrofuran structures corresponding to the core subunits of members of the Annonaceous acetogenin family of natural products. Transition-state models are proposed to account for the stereoselectivity of the double-stereodifferentiating [3 + 2]-annulation reactions.

subject areas

  • Acetogenins
  • Aldehydes
  • Allyl Compounds
  • Chelating Agents
  • Fatty Alcohols
  • Furans
  • Indicators and Reagents
  • Lactones
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Silanes
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo0511290

PubMed ID

  • 16277325
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Additional Document Info

start page

  • 8035

end page

  • 8046

volume

  • 70

issue

  • 20

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