ABSTRACT
This chapter deals with a fairly recent number of approaches to the synthesis of C-glycosides, the use of concerted processes. Fraser-Reid and Tulshian have employed a similar reaction for the synthesis of α-C-glycosides. Ireland has also converted a C-glycoside, that results from Ireland-Claisen rearrangement into the Prelog-Djerassi lactone. The Diels-Alder reaction, which is probably the most important reaction in organic chemistry, has also found application in C-glycoside synthesis. The work of Schmidt and co-workers15 illustrates the utility of hetero Diels-Alder for the preparation of aryl C-glycosides. There have been some reports involving cycloaddition reactions with the carbon portion of C-glycosides. The Ireland ester rearrangement has been used in several instances to quickly assemble C-glycosides to be used as synthetic intermediates in total synthesis. Cycloaddition chemistry has been used to prepare a C-substituted pyran ring that was further elaborated to a sugar like substance.
