Stereocontrolled synthesis of ara-type cyclohexenyl nucleosides.
A highly stereocontrolled synthesis of a new class of carbocyclic nucleosides, ara-type cyclohexenyl nucleosides, was developed. The key intermediate (+/-)-9 was obtained after a series of transformations starting from easily available endo-bicyclo carboxylic acid (+/-)-3. The allylic hydroxyl group of (+/-)-9 was masked via oxidation with manganese dioxide and released, after protection of the 2'-hydroxyl group, via reduction with NaBH(4) in the presence of CeCl(3).7H(2)O. The base moiety was introduced with use of the Mitsunobu methodology.
Wang
Jing
J
Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Belgium.
Viña
Dolores
D
Busson
Roger
R
Herdewijn
Piet
P
D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D002264:Carboxylic Acids; D007202:Indicators and Reagents; D009705:Nucleosides