Synthesis of 3',3'-difluoro-2'- hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides.
3',3'-Difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides 1-3 have been stereoselectively synthesized from ester 10, which can be conveniently prepared from 2,3-isopropylidene-d-glyceraldehyde 7 in five steps. The whole synthesis highlighted the stereoselective Reformatskii-Claisen rearrangement, ring-closing metathesis (RCM), and palladium-catalyzed allylic alkylation, in which the regioselectivity was reversed from that of nonfluorinated substrates.
Yang
Yan-Yan
YY
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Xu
Jun
J
You
Zheng-Wei
ZW
Xu
Xiu-Hua
XH
Qiu
Xiao-Long
XL
Qing
Feng-Ling
FL
D000478:Alkylation; D003500:Cyclization; D009705:Nucleosides / Q000138:chemical synthesis*
D009705:Nucleosides