Abstract
This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester 142 afforded adduct 130 as a single isomer. Transamination of compound 130, followed by cyclization provided lactam 147. The construction of C4 stereogenic center was achieved by the aldol reaction of boc-protected lactam 147 with acetone. Further functional group transformation led to the synthesis of (+)-2- epi-α-Allokainic acid 128.