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Hypervalent iodine(III)-promoted intermolecular C-C coupling of vindoline with β-ketoesters and related substrates

Academic Article
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Overview

authors

  • Turner, T. C.
  • Shibayama, K.
  • Boger, Dale

publication date

  • March 2013

journal

  • Organic Letters  Journal

abstract

  • The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free hypervalent iodine(III)-promoted intermolecular sp(3)/sp(2) coupling, representing a special class of selective C-H activation with direct carbon-carbon bond formation, proceeds with generation of a quaternary center capable of incorporation of the vinblastine C16' methyl ester and functionalized for subsequent divergent heterocycle introduction.

subject areas

  • Esters
  • Heterocyclic Compounds with 4 or More Rings
  • Iodine
  • Ketones
  • Molecular Structure
  • Nitriles
  • Stereoisomerism
  • Vinblastine
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Identity

PubMed Central ID

  • PMC3607625

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol400135n

PubMed ID

  • 23421318
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Additional Document Info

start page

  • 1100

end page

  • 1103

volume

  • 15

issue

  • 5

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