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New insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction

Academic Article
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Overview

related to degree

  • Sears, Justin, Ph.D. in Chemistry, Scripps Research 2010 - 2015

authors

  • Gotoh, Hiroaki
  • Sears, Justin
  • Eschenmoser, A.
  • Boger, Dale

publication date

  • August 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A definition of the scope of aromatic substrates that participate with catharanthine in an Fe(III)-mediated coupling reaction, an examination of the key structural features of catharanthine required for participation in the reaction, and the development of a generalized indole functionalization reaction that bears little structural relationship to catharanthine itself are detailed. In addition to providing insights into the mechanism of the Fe(III)-mediated coupling reaction of catharanthine with vindoline suggesting the reaction conducted in acidic aqueous buffer may be radical mediated, the studies provide new opportunities for the preparation of previously inaccessible vinblastine analogs and define powerful new methodology for the synthesis of indole-containing natural and unnatural products.

subject areas

  • Ferric Compounds
  • Molecular Structure
  • Vinblastine
  • Vinca Alkaloids
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Identity

PubMed Central ID

  • PMC3430138

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja306229x

PubMed ID

  • 22856867
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Additional Document Info

start page

  • 13240

end page

  • 13243

volume

  • 134

issue

  • 32

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