Unified strategy for the synthesis of C-aryl glycosides
S. F. Martin
Department of Chemistry and Biochemistry, The University
of Texas, Austin, TX 78712, USA
Abstract: 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.
*Lecture presented at the 14th International Conference
on Organic Synthesis (ICOS-14), Christchurch, New Zealand, 14-18 July
2002. Other presentations are published in this issue,
pp. 1-70.
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