Convenient synthesis of nucleoside and isonucleoside analogues.
[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.
Alvarez de Cienfuegos
Luis
L
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Campus de Fuentenueva 18071, Granada, Spain.
Mota
Antonio J
AJ
Robles
Rafael
R
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*
D007202:Indicators and Reagents; D009705:Nucleosides; D014498:Uracil; D003596:Cytosine; D013941:Thymine