Efficient synthesis of (2S,12′R)-2-(12′-aminotridecyl)pyrrolidine:: A defense alkaloid of the Mexican bean beetle

被引：0
|
作者：
Enders, D [1 ]
Thiebes, C [1 ]
机构：
[1] Rhein Westfal TH Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
来源：
SYNTHESIS-STUTTGART | 2000年 / 04期
关键词：
natural products; asymmetric synthesis; alkaloids nucleophilic 1,2-addition; SAMP/RAMP hydrazone method; pyrrolidines;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of (2S,12'R)-2-(12' -aminotridecyl)pyrrolidine [(S,R)-8], a defense alkaloid of the Mexican bean beetle Epilachna varivestis starting from (R)-proline is described. The second stereogenic center is generated by nucleophilic 1,2 addition of methyllithium to an aldehyde-SAMP-hydrazone, followed by reductive N-N bond cleavage. The product is obtained in good yield and high enantiomeric and diastereomeric purity.
引用
收藏
页码：510 / 512
页数：3
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