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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546

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Volume 75, Issue 1


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
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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.


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, Volume 75, Issue 1, Pages 63–70, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200375010063.

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