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Total syntheses of 2,2 '-epi-cytoskyrin a, rugulosin, and the alleged structure of rugulin

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

  • Nicolaou, K.C.
  • Lim, Yee Hwee
  • Piper, J. L.
  • Papageorgiou, C. D.

publication date

  • April 2007

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.

subject areas

  • Anthraquinones
  • Crystallography, X-Ray
  • Dimerization
  • Free Radicals
  • Models, Molecular
  • Molecular Structure
  • Naphthoquinones
  • Nitriles
  • Oxidation-Reduction
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0685708

PubMed ID

  • 17355133
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Additional Document Info

start page

  • 4001

end page

  • 4013

volume

  • 129

issue

  • 13

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