Synthesis of 2',3'-dideoxy-6',6'-difluorocarbocyclic nucleosides.
2',3'-Dideoxy-6',6'-difluorouracils, a novel series of gem-difluoromethylenated carbocyclic nucleosides, were synthesized from (Z)-but-2-ene-1,4-diol in 14 steps. A notable step was the construction of the carbocyclic ring via ring-closing metathesis and the incorporation of gem-difluoromethylene group by way of silicon-induced Reformatskii-Claisen reaction of chlorodifluoroacetic ester 3.
Yang
Yan-Yan
YY
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China.
Meng
Wei-Dong
WD
Qing
Feng-Ling
FL
D018360:Crystallography, X-Ray; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular
D015224:Dideoxynucleosides