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The Diels-Alder reaction in total synthesis

Academic Article
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Overview

related to degree

  • Snyder, Scott, Ph.D. in Chemistry, Scripps Research 1999 - 2004

authors

  • Nicolaou, K.C.
  • Snyder, Scott
  • Montagnon, T.
  • Vassilikogiannakis, G.

publication date

  • 2002

journal

  • Angewandte Chemie-International Edition  Journal

abstract

  • The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

subject areas

  • Catalysis
  • Chemistry, Organic
  • History, 20th Century
  • Models, Chemical
  • Nobel Prize
  • Organic Chemicals
  • Stereoisomerism
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Research

keywords

  • Diels-Alder reaction
  • biomimetic synthesis
  • cycloaddition
  • molecular diversity
  • total synthesis
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Identity

International Standard Serial Number (ISSN)

  • 1433-7851

Digital Object Identifier (DOI)

  • 10.1002/1521-3773(20020517)41:10<1668::aid-anie1668>3.0.co;2-z

PubMed ID

  • 19750686
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Additional Document Info

start page

  • 1668

end page

  • 1698

volume

  • 41

issue

  • 10

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