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Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B

Academic Article
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Overview

related to degree

  • Lim, Yee Hwee, Ph.D. in Organic Chemistry, Scripps Research , Joint graduate program with Oxford University 2005 - 2010

authors

  • Hayden, A. E.
  • Paton, R. S.
  • Becker, J.
  • Lim, Yee Hwee
  • Nicolaou, K.C.
  • Houk, K. N.

publication date

  • February 2010

journal

  • Journal of Organic Chemistry  Journal

abstract

  • The regioselectivities of several Diels-Alder reactions utilized en route to bisanthraquinone antibiotic BE-43472B are examined using density functional theory calculations. These reactions involve highly substituted dienes and juglone dienophiles, and there is an opposite regiochemical outcome for Diels-Alder reactions with beta-aryl substituted juglones when compared to reactions of unsubstituted juglone. In this article, the effect of an aromatic conjugating group bonded to juglone is explored.

subject areas

  • Anthraquinones
  • Anti-Bacterial Agents
  • Biological Products
  • Crystallography, X-Ray
  • Molecular Conformation
  • Molecular Structure
  • Naphthoquinones
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2813957

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo902572y

PubMed ID

  • 20027998
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Additional Document Info

start page

  • 922

end page

  • 928

volume

  • 75

issue

  • 3

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