title: Convenient synthesis of nucleoside and isonucleoside analogues.
abstract: [reaction: see text]. A very simple methodology to stereoselectively achieve tricyclic isonucleosides (nucleobase = thymine, uracil, and 5-fluoruracil) and 3'-C-branched nucleosides (nucleobase = theophylline) was performed by means of a DBU-mediated addition process using a readily available 2-bromo sugar. The mechanism for these transformations implies the loss of both substituents at C-2 and C-3 on the sugar moiety, and although it seems that DBU is probably involved, its involvement has not yet been ascertained. Cytosine did not react under these conditions.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus de Fuentenueva 18071, Granada, Spain.
authors.forename: Luis
authors.initials: L
authors.lastname: Alvarez de Cienfuegos
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Mota
authors.forename: Rafael
authors.initials: R
authors.lastname: Robles
mesh_terms: D002384:Catalysis; D003596:Cytosine / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013941:Thymine / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D009705:Nucleosides; D014498:Uracil; D003596:Cytosine; D013941:Thymine