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The University of Southampton
Chemistry

Research project: Rios: Asymmetric Synthesis of Natural Products and Pharmaceuticals

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Asymmetric synthesis is the intentional construction of enantiomers of a given constitutional isomer by means of chemical reactions. As Nobel laureate Sir John Warcup Conforth quoted: “the versatility and power of modern synthetic methods, acting on information provided by modern analytical methods and motivated by the economic importance of the target, can be invaluable”. For this reason in our research group we devoted our efforts in the development of new asymmetric methodologies for the synthesis of complex scaffolds. Moreover some of our methodologies are focused in the synthesis of Natural products or biologically interesting compounds.

Recently we have developed a cascade reaction for the synthesis of a-methylene lactones. Initial biological testing of the synthesized compounds reported promising activities against human leukemia HL-60 cell line.1

Figure 1
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We also reported the synthesis of (-)-paroxetine and (+)-Femoxetine. We developed a new Michael-hemiaminal formation cascade reaction that allow us to build the core of these pharmaceutical in highly enantioselective fashion.2,3

Figure 2
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Related Publications:

1 “First One-pot organocatalytic synthesis of a-methylene-y-lactones” Xavier Companyó, A. Moyano, A. Mazzanti, A. Janecka, R. Rios* Chem. Commun. 2013, 49(12), 1184-1186. Highlighted in Synfacts (Synfacts; 02, 2013)

2 “Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines” S. Číhalová, G. Valero, J. Schimer, M. Humpl, M. Dračínský, A. Moyano, R. Rios,* and J. Vesely*, Tetrahedron 2011, 67, 8942-8950. Highlighted in Synfacts (Synfacts; 01, 2012)

3 “Highly enantioselective organocatalitic synthesis of piperidines. Formal synthesis of (-)-Paroxitene”. G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, R. Rios. Tetrahedron Letters 2009, 50, 1943-1946.

Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow
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