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Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure

Academic Article
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Overview

authors

  • Roush, William
  • Neitz, R. J.

publication date

  • July 2004

journal

  • Journal of Organic Chemistry  Journal

abstract

  • The originally proposed structure (2) of landomycinone, the aglycone of landomycin A, has been synthesized and shown to be nonidentical to the naturally derived landomycin A aglycone. The synthesis of 2 features the Dötz benzannulation reaction of chromium carbene 5 and alkyne 6, and the intramolecular Michael-type cyclization reaction of the phenolic naphthoquinone 20. It is proposed that natural landomycinone possesses the alternative structure 3, but attempts to access this structure via the Michael-type cyclization of the isomeric phenolic naphthoquinone 38 have been unsuccessful.

subject areas

  • Aminoglycosides
  • Carbohydrate Sequence
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Molecular Sequence Data
  • Naphthoquinones
  • Oligosaccharides
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo049426c

PubMed ID

  • 15255715
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Additional Document Info

start page

  • 4906

end page

  • 4912

volume

  • 69

issue

  • 15

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