Synthesis of the optical isomers of a new anticholinergic drug, penehyclidine hydrochloride (8018)

Xiang-Yu Han; He Liu; Chun-He Liu; Bo Wu; Lan-Fu Chen; Bo-Hua Zhong; Ke-Liang Liu

doi:10.1016/j.bmcl.2005.02.071

Synthesis of the optical isomers of a new anticholinergic drug, penehyclidine hydrochloride (8018)

Bioorg Med Chem Lett. 2005 Apr 15;15(8):1979-82. doi: 10.1016/j.bmcl.2005.02.071.

Authors

Xiang-Yu Han¹, He Liu, Chun-He Liu, Bo Wu, Lan-Fu Chen, Bo-Hua Zhong, Ke-Liang Liu

Affiliation

¹ No. 7 Department, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, PR China. han_xiangyu@yahoo.com.cn <han_xiangyu@yahoo.com.cn>

PMID: 15808451
DOI: 10.1016/j.bmcl.2005.02.071

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cholinergic Antagonists / chemical synthesis*
Cyclopentanes / chemical synthesis*
Quinuclidines / chemical synthesis*
Stereoisomerism

Substances

Cholinergic Antagonists
Cyclopentanes
Quinuclidines
3-(2'-phenyl-2'-cyclopentyl-2'-hydroxyethoxy)quinuclidine