Abstract
This thesis describes the application of imine 135 that derived from the condensation of ketopinic amide 168, a chiral auxiliary, and tert-butyl glycinate 171 in the synthesis of pyrrolidine alkaloids. Asymmetric Michael addition of imine 135 with α,β-unsaturated ester 149 afforded adduct 159 as a diastereomeric mixture (>20 : 1). Transamination of adduct 159, followed by cyclization provided lactam 179. The construction of C4 stereogenic center was achieved by aldol reaction of Boc-protected lactam 179 with activated acetone. Further functional group transformations afforded compound 189 which is an important precursor for the synthesis of (+)-α-allokainic acid 22.