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Synfacts 2014; 10(1): 0007
DOI: 10.1055/s-0033-1340326
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Levamisole

Contributor(s):
Philip Kocienski
Sadhukhan A, Sahu D, Ganguly B, * Khan NH, * Kureshy RI, Abdi SH. R, Suresh E, Bajaj HC. Central Salt & Marine Chemicals Research Institute, Bhavnagar, India
Oxazoline-Based Organocatalyst for Enantioselective Strecker Reactions: A Protocol for the Synthesis of Levamisole.

Chem. Eur. J. 2013;
19: 14224-14232
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

levamisole - asymmetric Strecker reaction - α-aminonitriles - organocatalysis - 1,2-diamines

Significance

Levamisole (Ergamisol®) is an ­antihelminthic that is currently used to treat worm infestations in livestock. The synthesis of levamisole depicted features an asymmetric Strecker reaction of N-benzhydryl aldimine A with trimethylsilyl cyanide catalyzed by oxazoline (R,R)-B (5 mol%) as the key step. The chiral α-aminonitrile intermediate C was generated in 90% yield and 90% ee.


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Comment

A study of the scope of the asymmetric Strecker reaction (18 examples) revealed that both alkyl and aryl N-benzhydryl aldimines participate in the reaction to give the corresponding α-aminonitriles in good yield and generally >80% ee with some exceptions being shown in the box above. For a previous synthesis of levamisole based on asymmetric diamination of styrenes, see: C. Röben et al. Angew. Chem. Int. Ed. 2011, 50, 9478.


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