Muray Elena, Rifé Joan, Branchadell Vicenç, Ortuño Rosa M
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona, Spain.
J Org Chem. 2002 Jun 28;67(13):4520-5. doi: 10.1021/jo025599v.
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.
描述了合成新型环丙基碳环核苷的通用且立体可控的方法。目标产物是由合适的环丙烷前体合成的，这些前体又依次从以D-甘油醛为手性前体衍生的烯烃化合物获得。官能团的选择性操作使得制备对映体纯的核苷成为可能，其中一些显示出相反的手性。所有这些分子在环丙烷环的C-1或C-3处含有一个季碳手性中心，并带有一个氨基、一个羟甲基或一个甲基作为额外的取代基。在一个实例中，胸腺嘧啶直接与环丙烷相连。在其他合成的核苷中，亚甲基单元用作间隔基。
