Synthesis of the optical isomers of a new anticholinergic drug, penehyclidine hydrochloride (8018).
A practical diastereoselective synthetic method for 8018 enantiopure isomers is described. The intramolecular asymmetric epoxidation of mono-sulfonate 4 was applied for the execution of the synthesis of the key chiral building block for the first time. The isomers were obtained with 70-76% yields in 99-100% ee.
Han
Xiang-Yu
XY
No. 7 Department, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, PR China. han_xiangyu@yahoo.com.cn <han_xiangyu@yahoo.com.cn>
Liu
He
H
Liu
Chun-He
CH
Wu
Bo
B
Chen
Lan-Fu
LF
Zhong
Bo-Hua
BH
Liu
Ke-Liang
KL
D018680:Cholinergic Antagonists / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D011812:Quinuclidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D018680:Cholinergic Antagonists; D003517:Cyclopentanes; D011812:Quinuclidines; C066419:3-(2'-phenyl-2'-cyclopentyl-2'-hydroxyethoxy)quinuclidine