UCO2M, UMR CNRS 6011, Faculté de Sciences et Techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
J Org Chem. 2011 Oct 7;76(19):8059-63. doi: 10.1021/jo2012708. Epub 2011 Sep 6.
The asymmetric synthesis of novel cyclohexene nucleoside analogues 12 and 15 is described. An enantiospecific Diels-Alder reaction between (E,E)-diene 2 and (+)-5-(d-mentyloxy)-2(5H)-furanone 3 provided the cycloadduct isomer 4. Three additional steps yielded amine 8 allowing the constructions of the thymine and adenine moieties to afford intermediates 11 and 14, respectively. Amination or cyclization and removal of the protecting groups occurred in one step in the presence of ammonia, giving the target six-membered ring nucleosides.
描述了新型环己烯核苷类似物 12 和 15 的不对称合成。（E，E）-二烯 2 和（+）-5-（d-薄荷氧基）-2（5H）-呋喃酮 3 之间的对映选择性 Diels-Alder 反应提供了环加成异构体 4。通过三个额外的步骤得到胺 8，允许构建胸腺嘧啶和腺嘌呤部分，分别得到中间体 11 和 14。在氨的存在下，通过一步反应进行氨化或环化和脱保护基，得到目标六元环核苷。
