An efficient and stereodefined strategy is described for the first asymmetric synthesis of a new type of pyrrolizidine alkaloids, amphorogynine A and its 1-epi-isomer. The key 2,4-disubstituted pyrrolidine ring was constructed by elaboration of the chiral lactam derivative incorporating the D-malic acid-derived skeleton through asymmetric cis-allylation of the functionalized allysilane. © 2003 Elsevier Science Ltd. All rights reserved.