The total synthesis of C-glycosides by cycloaddition reactions

C-glycosides play important roles in biological processes. Synthetic efforts to prepare carbohydrate mimetics—C-glycosides were undertaken. This thesis introduces the total syntheses of C-glycosides by starting with two cycloaddition reactions. The [4+2] reaction of 1,3-pentadiene with glyoxylic acid and subsequent reactions afforded five C-pyranosides. The [4+3] cycloaddition of furan and pentachloroacetone and subsequent reactions provided C-furanosides and C-pyranosides. A new type of C-disaccharide mimetic coupled by an amide bond was synthesized.; This thesis describes how bromolactonization, stereoselective Beckmann rearrangement and stereoselective dechlorination were used in a new way to fulfill the research goal. This dissertation provides efficient ways to synthesize carborhydrate mimetics from cheap, easily available non-natural materials.