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Pure Appl. Chem., 2001, Vol. 73, No. 3, pp. 573-578

Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

Dieter Enders* and Christoph Thiebes

Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany

Abstract: Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.