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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

12 Issues per year


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1365-3075
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Volume 75, Issue 1 (Jan 2003)

Issues

Unified strategy for the synthesis of C-aryl glycosides

S. F. Martin
  • Corresponding author
  • Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712, USA
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200375010063

A unified approach for the synthesis of the four major groups of C-aryl glycosides has been developed. The strategy incorporates two integrated approaches, the first of which features the [4+2] cycloaddition of a glycosyl furan with a substituted benzyne followed by the acid-catalyzed opening of the resultant adduct. The second route involves the sequential palladium-catalyzed opening of a benzyne-furan cycloadduct with an iodo glycal followed by oxidation of the resultant dihydronaphthol ring and reduction of the glycal moiety. The utility of this strategy has been established by a concise formal synthesis of the C-aryl glycoside antibiotic galtamycinone.

Conference

International Conference on Organic Synthesis (ICOS-14), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 14th, Christchurch, New Zealand, 2002-07-14–2002-07-18

About the article

Published Online: 2009-01-01

Published in Print: 2003-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200375010063.

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