Bioactive Heterocycles II

Volume 8 of the series Topics in Heterocyclic Chemistry pp 73-97


Synthesis of Thalidomide

  • Norio ShibataAffiliated withGraduate School of Engineering, Nagoya Institute of Technology Email author 
  • , Takeshi YamamotoAffiliated withGraduate School of Engineering, Nagoya Institute of Technology
  • , Takeshi ToruAffiliated withGraduate School of Engineering, Nagoya Institute of Technology Email author 

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Despite the most notorious medical disaster caused by thalidomide in medical history, huge numbers of papers have been published about this drug since its formulation in 1956. While most of the early studies specifically concerned teratogenicity, recently there has been a resurgence of interest in thalidomide because of its potential for treating a number of otherwise intractable diseases, such as leprosy, human immunodeficiency virus replication in acquired immune deficiency syndrome, and cancer. Although the pharmacological aspects of the drug have been frequently reviewed, reviews focusing on thalidomide synthesis are rare. Here, the synthesis of thalidomide is reviewed in chronological order from the first report. We first aim to give an overview of the most conventional aspects of thalidomide. Subsequently, we will focus on the synthesis of racemic thalidomide, which is now commercially available. Finally, we will describe the asymmetric synthesis of thalidomide. To our knowledge, all the papers and patents concerning thalidomide synthesis have been introduced. Because of the number of papers and patents, we will not mention the preparation of thalidomide derivatives.
Asymmetric synthesis Drug synthesis Teratogenicity Thalidomide