Abstract

Short, highly stereocontrolled, asymmetric total syntheses of the title amphibian alkaloids are described. In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form. This short sequence proceeds in five laboratory operations and involves the novel intermediacy of an «unprotected» 2-acylpyrrolidine intermediate (Scheme VII). The (Z)-alkylidene side chain of the target alkaloids are introduced by stereocontrolled aldol dehydration sequences (Schemes X and XI)

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