杀结核菌素的全合成研究
收稿日期: 2014-02-23
修回日期: 2014-03-20
网络出版日期: 2014-04-10
基金资助
国家自然科学基金（Nos.20962009，21062006）、教育部新世纪优秀人才支持计划（No.11-1000）、江西省青年科学家培养对象项目和南昌市科技局资助项目.
An Improved Total Synthesis of Tubercidin
Received date: 2014-02-23
Revised date: 2014-03-20
Online published: 2014-04-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20962009, 21062006), the Program for New Century Excellent Talents in University (No. 11-1000), the Training Project of Jiangxi Youth Scientists and the Bureau of Science & Technology of Nanchang City.
黄海洋 , 阮志忠 , 胡韬 , 肖强 . 杀结核菌素的全合成研究[J]. 有机化学, 2014 , 34(7) : 1358 -1363 . DOI: 10.6023/cjoc201402027
Tubercidin is a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside with significantly biological activities, such as anti-schistosomal, antibacterial and antitumor. An improved total synthesis of tubercidin is reported using microwave promoted Vorbrüggen glycosylation as the key step. Thus, tubercidin was synthesized in 3 steps with 74% overal yield using 6-chloro-7-bromo-pyrrolo[2,3-d]pyrimidine and 1-O-acetyl-2,3,5-O-tribenzoyl-β-D-ribose as starting materials. The applica- tion of micromave irridated one-pot reaction is also reported in the synthesis of 7-deazapurine nucleosides using potassium nonafluoro-1-butanesulfonate, trimethylsilyl chloride and silylation reagent [hexamethyldisilazane or N,O-bis(trimethyl- silyl)acetamide].
Key words： nucleoside; total synthesis; natural product; glycosylation; microwave
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