Total Synthesis of Entecavir
Javier Velasco(Universitat de Barcelona), Xavier Ariza(Institut de Biomedicina de la Universitat de Barcelona), Laura Badía(Esteve Química (Spain)), Martí Bartra(Esteve Química (Spain)), Ramon Berenguer(Esteve Química (Spain)), Jaume Farràs(Institut de Biomedicina de la Universitat de Barcelona), Joan Gallardo(Universitat de Barcelona), Jordi García(Institut de Biomedicina de la Universitat de Barcelona), Yolanda Gasanz(Esteve Química (Spain))
Cited by 43Open Access
Abstract
Entecavir (BMS-200475) was synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (i) a stereoselective boron-aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (ii) its cyclization by a Cp2TiCl-catalyzed intramolecular radical addition of an epoxide to an alkyne; and (iii) the coupling with a purine derivative by a Mitsunobu reaction.
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