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Concise total synthesis of two marine natural nucleosides: trachycladines A and B.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2014 , DOI: 10.3762/bjoc.10.176
Haixin Ding 1 , Wei Li 1 , Zhizhong Ruan 1 , Ruchun Yang 1 , Zhijie Mao 1 , Qiang Xiao 1 , Jun Wu 2
Affiliation  

We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-beta-D-ribofuranose as the starting material. The critical step was the SnCl4 assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.

中文翻译:

两种海洋天然核苷的简明全合成:trachycladines A 和 B。

我们报告了使用 5-脱氧-1,2,3-三-O-乙酰-β-D 首次全合成 trachycladines A(10 步,34.2% 总产率)和 B(11 步,35.0% 总产率) -呋喃核糖作为起始原料。关键步骤是 SnCl4 辅助过苄基化 1-O-甲基-5-脱氧呋喃核糖的区域选择性和立体选择性脱保护。酶腺苷酸脱氨酶 (EC 3.5.4.6) 已成功应用于 trachycladines B 的化学酶法合成。
更新日期:2017-01-31
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