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Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids

Academic Article
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Overview

related to degree

  • Deechongkit, Songpon, Ph.D. in Organic Chemistry, Scripps Research 1999 - 2003

authors

  • You, S. L.
  • Deechongkit, Songpon
  • Kelly, Jeffery

publication date

  • 2004

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] The solid-phase assembly of heterocyclic amino acids enabled the total synthesis of numerous diastereoisomers of tenuecyclamides A-D, establishing or correcting the stereochemistry of each natural product. This strategy provides a very efficient route to synthesize thiazole- and oxazole-containing macrolactams from heterocyclic amino acids that are readily prepared from Fmoc-alpha-amino acids. This methodology appears to be broadly applicable to the synthesis of natural product libraries incorporating unnatural heterocyclic amino acid residues for the purpose of drug discovery.

subject areas

  • Amino Acids
  • Catalysis
  • Indicators and Reagents
  • Molecular Structure
  • Peptides, Cyclic
  • Stereoisomerism
  • Thiazoles
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol049020m

PubMed ID

  • 15255707
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Additional Document Info

start page

  • 2627

end page

  • 2630

volume

  • 6

issue

  • 15

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