Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

被引:96
|
作者
Enders, D [1 ]
Thiebes, C [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1351/pac200173030573
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 alpha -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.
引用
收藏
页码:573 / 578
页数:6
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