Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada.
Molecules. 2010 May 26;15(6):3816-28. doi: 10.3390/molecules15063816.
The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an alpha-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.
报告了两种核苷类似物的制备。这两种合成都涉及环丁酮的关键光化学反应环扩张为氧杂碳烯及其随后被 6-氯嘌呤清除。双环（锁定）嘌呤的合成从带有羟甲基侧链的氧杂双环庚酮开始。异核苷的制备使用带有α取代的 6-氯嘌呤的环丁酮。后者的辐照产生异核苷和非环核苷类似物。
