ABSTRACT
This chapter addresses the synthetic approaches to naturally occurring aryl C-glycosides. The sequence begins with the thioglycoside 143 that was transformed into 144 by protection and oxidation. The vineomycin class of antibiotics are a class of aryl C-glycosides that were isolated from Streptomyces matensis vineus by Omura and co-workers. Many synthetic approaches have been reported to this natural product, and in doing so have avoided the issue of C-glycoside formation. More traditional methods such as condensations with aryl Grignards or aryl lithiums have also found their place in aryl C-glycoside natural product synthesis. In one case, an existing alkyl C-glycoside was further transformed into an aryl C-glycoside. Yamaguchi and co-workers employed an original approach to the synthesis of this aryl C-glycoside. They chose to begin with an alkyl C-glycoside and convert it, through the use of polyketide condensation reactions, to the target.
