Todd:Pictet-Spengler to PZQ

Home        Contact        Internal        People        Papers        Research        Teaching        Links        News        Construction       

Pictet-Spengler route to Praziquantel

Michael Woelfle,¹ and Matthew H. Todd¹*
1. School of Chemistry, The University of Sydney, NSW 2006, Australia

• To whom correspondence should be addressed: Tel. +61 2 9351 2180, matthew.todd@sydney.edu.au

Abstract

The Pictet-Spengler route to Praziquantel

The PZQ precursor

By using the Ugi reaction

Results

Synthesis of the catalysts

1,1-Binaphthyl-2,2-disulfonate

1. Step: Preparation of 1,1’-Binaphthalene-2,2’-diyl-O,O’-bis(N,N’-dimethylthiocarbamate) (MW45-1)

2. Step: Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)

3. Step: Preparation of 1,1’-Binaphthalene-2,2’-disulfonic acid (MW45-3)

• Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction, M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858–16860; DOI: 10.1021/ja806875c.

• A Powerful Chiral Counteranion Motif for Asymmetric Catalysis, P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363 –4366; DOI: 10.1002/anie.200901768.

References

• Synthesis of Praziquantel, J. H. Kim, Y. S. Lee, H. Park and C. S. Rim, Tetrahedron , 1998, 54, 7395-7400. (DOI: doi:10.1016/S0040-4020(98)00401-3)

• Novel Synthesis of Praziquantel, A. Dömling, Patent Application 2009, WO 2009/11533(A1), Language: German.