Convenient synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist

被引：7

作者：

Ezawa, Tetsuya ^{[1
]}

Kawashima, Yuya ^{[1
]}

Noguchi, Takuya ^{[1
]}

Jung, Seunghee ^{[1
]}

Imai, Nobuyuki ^{[1
]}

机构：

[1] Chiba Inst Sci, Fac Pharm, 15-8 Shiomi Cho, Choshi, Chiba 2880025, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 02期

关键词：

PORCINE PANCREAS LIPASE; CATALYTIC ENANTIOSELECTIVE CYCLOPROPANATION; AMYOTROPHIC-LATERAL-SCLEROSIS; DISULFONAMIDE LIGAND; PEPTIDE-SYNTHESIS; ALLYLIC ALCOHOLS; INDUCED TOXICITY; BINDING-SITES; AMINO-ACIDS; DRUGS;

D O I：

10.1016/j.tetasy.2016.12.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We have achieved a convenient enantioselective synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist in 19-40% overall chemical yields from the corresponding 2-arylbut-2-ene-1,4-diols with moderate to excellent asymmetric yields via regioselective acetylation using porcine pancreas lipase, catalytic enantioselective Simmons-Smith reactions, and amidation in aqueous organic solvent. This synthetic route is more efficient and less expensive than conventional methods. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：266 / 281

页数：16

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