Referenced in: none

Automatically associated channels: Kir2.3

Title: Synthesis of (-)-epibatidine and its derivatives from chiral allene-1,3-dicarboxylate esters.

Authors: Hiroyuki Kimura, Toshio Fujiwara, Takahiro Katoh, Kiyoharu Nishide, Tetsuya Kajimoto, Manabu Node

Journal, date & volume: Chem. Pharm. Bull., 2006 Mar , 54, 399-402

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/16508202

Abstract
(-)-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.