Kimura Hiroyuki, Fujiwara Toshio, Katoh Takahiro, Nishide Kiyoharu, Kajimoto Tetsuya, Node Manabu
Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Misasagi, Japan.
Chem Pharm Bull (Tokyo). 2006 Mar;54(3):399-402. doi: 10.1248/cpb.54.399.
(-)-Epibatidine, an excellent candidate of non-opioidal anesthesia, was formally synthesized in short steps from di-(l)-menthyl (R)-allene-1,3-dicarboxylate that was facilely prepared as a single isomer by means of crystallization-induced asymmetric transformation from a diastereomer mixture of (R)- and (S)-allene-1,3-dicarboxylates. Taking advantage of the chiral synthesis, derivatives of (-)-epibatidine were also prepared for targeting diagnostic agents that could bind nicotinic acetylcholine receptors (nAChRs) in the mammalian central nerve system.
（-）-表蝙蝠毒素是一种非阿片类麻醉的优秀候选物，它以简短的步骤从（R）-1,3-丙二烯二甲酸二（L）-薄荷酯正式合成，该酯通过从（R）-和（S）-1,3-丙二烯二甲酸酯的非对映异构体混合物中通过结晶诱导的不对称转化轻松制备为单一异构体。利用手性合成，还制备了（-）-表蝙蝠毒素的衍生物，以靶向可与哺乳动物中枢神经系统中的烟碱型乙酰胆碱受体（nAChRs）结合的诊断剂。
