• Professor P. Quadrelli (University of Pavia, Italy)

    Professor P. Quadrelli (University of Pavia, Italy)

     

Synthesis of N,O-nucleosides via an Ene Reaction

Paolo Quadrelli presents the synthesis of N,O-nucleosides from (nitrosocarbonyl)mesitylene.

N,O-Nucleosides from Ene Reaction of (Nitrosocarbonyl)mesitylene with Crotyl Alcohol: Selectivity, Scope, and Limitations: S. Carosso, M. G. Memeo, B. Bovio, E. Valletta, B. Macchi, P. Quadrelli
Synthesis 2017, 49, DOI: 10.1055/s-0036-1588695

The importance of nucleoside analogues in a number of areas of drug discovery and chemical biology continues to act as a spur to develop practical and efficient synthetic methods for accessing these compounds. Recently, the group of Professor Paolo Quadrelli at the University of Pavia (Italy) devised and reported a new strategy relying on the ene reaction for preparing N,O-nucleosides.

  • Synthesis of N,O-nucleosides via an ene reaction

    Synthesis of N,O-nucleosides via an ene reaction

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Professor Quadrelli said: 

“Sterically encumbered nitrosocarbonyl intermediates react with allylic alcohols and are able to activate the route towards 5-hydroxyisoxazolidines. These heterocycles are easily functionalized with a variety of heterobases and their biological behavior against several viruses as well as the potential apoptotic activities are actually investigated in collaboration with international research groups.” 

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