Synthesis 2018; 50(02): 211-226
DOI: 10.1055/s-0036-1590938
short review
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthetic Strategies of (R)-(–)-Baclofen: An Antispastic Drug

CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, Telangana, India   Email: chemryams@gmail.com
,
Devatha Suman
CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, Telangana, India   Email: chemryams@gmail.com
,
Koti Siva Nagi Reddy
CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, Telangana, India   Email: chemryams@gmail.com
› Author Affiliations
D.S. and K.S.N.R. thank the Council of Scientific and Industrial Research­, New Delhi for financial assistance in the form of a fellowship. P. R. thanks the Council of Scientific and Industrial Research, Ministry of Science and Technology, New Delhi, for funding the project ORIGIN (CSC-0108).
Further Information

Publication History

Received: 11 July 2017

Accepted after revision: 26 September 2017

Publication Date:
20 October 2017 (online)

Dedicated to Dr. Nitin W. Fadnavis, Natural Products Chemistry Division, IICT, Hyderabad on the occasion of his 63rd birthday

Abstract

Baclofen is an antispastic drug used as a muscle relaxant in the treatment of the paroxysmal pain of trigeminal neuralgia, spasticity of the spinal cord and cerebral origin. Baclofen resides biological activity exclusively in its (R)-(–)-enantiomer. In this review, various asymmetric synthetic strategies for (R)-(–)-baclofen are described.

1 Introduction

2 Resolution Synthetic Approaches

2.1 Chemical Resolution

2.2 Biocatalytic Resolution

3 Asymmetric Desymmetrization

3.1 Catalytic Enantioselective Desymmetrization

3.2 Enzymatic Desymmetrization

4 Chiral Auxiliary Induced Asymmetric Synthesis

4.1 Asymmetric Michael Addition

4.2 Asymmetric Aldol Addition

4.3 Asymmetric Nucleophilic Substitution

5 Asymmetric Reduction

5.1 Catalytic Asymmetric Hydrogenation

5.2 Bioreduction

6 Catalytic Asymmetric Conjugate Addition

7 Conclusion

 
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