Pure Appl. Chem., 2003, Vol. 75, No. 1, pp. 63-70
doi:10.1351/pac200375010063
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.