Stereoselective synthesis of novel types of cyclopropyl carbocyclic nucleosides containing quaternary stereogenic centers.
Versatile and stereocontrolled synthetic entries to novel types of cyclopropyl carbocyclic nucleosides are described. The target products have been synthesized from suitable cyclopropane precursors obtained, in turn, from olefinic compounds derived from D-glyceraldehyde as a chiral precursor. Selective manipulation of the functional groups has allowed the preparation of enantiopure nucleosides, some of them displaying opposite chirality. All these molecules contain a quaternary stereogenic carbon at C-1 or C-3 of the cyclopropane ring and bear an amino, a hydroxymethyl, or a methyl group as an additional substituent. In one instance, thymine is directly linked to the cyclopropane. A methylene unit serves as the spacer in the other synthesized nucleosides.
Muray
Elena
E
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona, Spain.
Rifé
Joan
J
Branchadell
Vicenç
V
Ortuño
Rosa M
RM
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D005985:Glyceraldehyde / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D003521:Cyclopropanes; D009705:Nucleosides; D005985:Glyceraldehyde