An Enantioselective Approach to Functionalized Amino Acids: Total Synthesis of Antiepileptic Drug (R)-Lacosamide

被引：25

作者：

Garg, Yuvraj ^{[1
]}

Pandey, Satyendra Kumar ^{[1
]}

机构：

[1] Thapar Univ, Sch Chem & Biochem, Patiala 147001, Punjab, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 08期

关键词：

ANTICONVULSANT ACTIVITIES; ASYMMETRIC-SYNTHESIS; LACOSAMIDE; DERIVATIVES; EPILEPSY;

D O I：

10.1021/acs.joc.5b00480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and highly efficient synthetic approach to enantiopure functionalized amino acids (FAAs) 1 skeleton from racemic butadiene monoepoxide as a starting material and its application to the total synthesis of an antiepileptic drug (R)-lacosamide 2 are described. The synthesis utilizes the palladium catalyzed Trosts Dynamic Kinetic Asymmetric Transformation (DYKAT) as key step.

引用

页码：4201 / 4203

页数：3

共 39 条

[1] Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives [J].

Andurkar, SV ;

Stables, JP ;

Kohn, H .

TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3841-3854

[2]

[Anonymous], 2008, WPA WRITING PROGRAM

[3]

[Anonymous], COCHRANE DATABASE SY

[4]

Anumula R. R., 2011, Patent, Patent No. [2011130615, WO2011130615A2]

[5]

Benjamin RT, 2003, ORG LETT, V5, P1031, DOI [10.1021/ol0340078, DOI 10.1021/OL0340078]

[6]

Bernaz-Vazquez P. M., 2013, Patent, Patent No. [WO2013030654A1, 2013030654, WO 2013030654 A1]

[7] Lacosamide: pharmacology, mechanisms of action and pooled efficacy and safety data in partial-onset seizures [J].

Beydoun, Ahmad ;

D'Souza, Joseph ;

Hebert, David ;

Doty, Pamela .

EXPERT REVIEW OF NEUROTHERAPEUTICS, 2009, 9 (01) :33-42

[8]

Biswas S., 2014, Process for the Preparation of Lacosamide Using Novel Intermediates, Patent No. [WO 2014155264 A1, 2014155264, WO2014155264A1]

[9]

Bologna A., 2013, Patent US, Patent No. 20130030216

[10]

Bosch I L. J., 2011, Patent, Patent No. [WO2011158194, 2011158194]

← 1 2 3 4 →