Todd:Pictet-Spengler to PZQ: Difference between revisions
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(New page: {{Todd}} =Pictet-Spengler route to Praziquantel= Michael Woelfle,<sup>1</sup> and Matthew H. Todd<sup>1</sup>*<br> 1. School of Chemistry, The University of Sydney, NSW 2006, Australia<b...) |
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==Abstract== | ==Abstract== | ||
The Pictet-Spengler route to Praziquantel | |||
The PZQ precursor | |||
By using the Ugi reaction | |||
==Introduction== | ==Introduction== | ||
==Results== | ==Results== | ||
===Preparation of the Ugi-intermediates== | |||
===Synthesis of the catalysts=== | |||
'''1,1-Binaphthyl-2,2-disulfonate''' | |||
1. Step: [http://www.ourexperiment.org/racemic_pzq/567 Preparation of 1,1’-Binaphthalene-2,2’-diyl-O,O’-bis(N,N’-dimethylthiocarbamate) (MW45-1)] | |||
2. Step: [http://www.ourexperiment.org/racemic_pzq/583 Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)] | |||
3. Step: [http://www.ourexperiment.org/racemic_pzq/587 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; [http://dx.doi.org/10.1021/ja806875c 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; [http://www3.interscience.wiley.com/journal/122382952/abstract DOI: 10.1002/anie.200901768]. | |||
==References== | ==References== | ||
* Synthesis of Praziquantel, J. H. Kim, Y. S. Lee, H. Park and C. S. Rim, Tetrahedron , 1998, 54, 7395-7400. ([http://dx.doi.org/10.1016/S0040-4020(98)00401-3 DOI: doi:10.1016/S0040-4020(98)00401-3]) | |||
* [http://v3.espacenet.com/publicationDetails/biblio?CC=WO&NR=2009115333A1&KC=A1&FT=D&date=20090924&DB=EPODOC&locale=en_ep Novel Synthesis of Praziquantel, A. Dömling, Patent Application 2009, WO 2009/11533(A1), Language: German.] | |||
Revision as of 22:34, 24 May 2011
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
Introduction
Results
=Preparation of the Ugi-intermediates
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)
