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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Unified strategy for the synthesis of C-aryl glycosides
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
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