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Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives

Academic Article
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Overview

related to degree

  • Castle, Steven Lane, Ph.D. in Chemistry, Scripps Research 1995 - 2000
  • Zhou, Jiacheng, Ph.D. in Chemistry, Scripps Research 1991 - 1996

authors

  • Boger, Dale
  • Zhou, Jiacheng
  • Borzilleri, R. M.
  • Nukui, S.
  • Castle, Steven Lane

publication date

  • 1997

journal

  • Journal of Organic Chemistry  Journal

abstract

  • Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo961346o

PubMed ID

  • 11671510
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Additional Document Info

start page

  • 2054

end page

  • 2069

volume

  • 62

issue

  • 7

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