title: Total synthesis of entecavir.
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.
authors.affiliation: Departament de Química Orgànica and Institut de Biomedicina de la Universitat de Barcelona (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1, 08028-Barcelona, Spain.
authors.forename: Javier
authors.initials: J
authors.lastname: Velasco
authors.forename: Xavier
authors.initials: X
authors.lastname: Ariza
authors.forename: Laura
authors.initials: L
authors.lastname: Badía
authors.forename: Martí
authors.initials: M
authors.lastname: Bartra
authors.forename: Ramon
authors.initials: R
authors.lastname: Berenguer
authors.forename: Jaume
authors.initials: J
authors.lastname: Farràs
authors.forename: Joan
authors.initials: J
authors.lastname: Gallardo
authors.forename: Jordi
authors.initials: J
authors.lastname: Garcia
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Gasanz
mesh_terms: D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C413685:entecavir; D006147:Guanine