两种3-甲基吡咯烷蚂蚁毒素的不对称合成  

Alternative Asymmetric Synthesis of Two Venom Alkaloids of Ants Leptothoracini (Myrmicinae)

作　　者：郑啸[1] 阮源萍[1] 黄培强[1] 

机构地区：[1]厦门大学化学系,福建厦门361005

出　　处：《厦门大学学报（自然科学版）》2004年第1期67-70,共4页Journal of Xiamen University：Natural Science

基　　金：国家自然科学基金(29832020)资助

摘　　要：以(S) 苹果酸衍生出的(2S,3R) 3 甲基苹果酸二甲酯7为原料,经过氯代、自由基还原脱氯和酯基还原得到(R) 2 甲基 1,4丁二醇10,对映体纯度为79.7%ee.进而合成了蚂蚁信息素生物碱(R) Leptothoracine1和(R) N (2' 苯基乙基) 3 甲基吡咯烷2.An alternative asymmetric synthesis of ant venom alkaloids (R)-Leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine 2 are described. The synthesis was achieved by replacement of the hydroxyl group of dimethyl (2S, 3R)-3-methylmalate 7 with chloride, followed by radical dechlorination and ester reduction, which afforded (R)-2-methyl-1,4-butanediol 10 in 79.7 % ee. Diol 10 was further transformed into the natural enantiomer of ant venom alkaloids (R)-Leptothoracine 1 and 2 by usual bis-tosylation and amination procedures.

关 键 词：3-甲基吡咯烷蚂蚁毒素 不对称合成 (s)-苹果酸 生物碱 吡咯烷 蚂蚁信息素 

分 类 号：O626.13[理学—有机化学] O621.34[理学—化学]