Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: Effects of the bulky protecting groups to enforce facial selectivity
Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: Effects of the bulky protecting groups to enforce facial selectivity
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DOI：
10.1021/jo0356762
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发表时间：
2004-04-02
影响因子：
3.6
通讯作者：
Jeong, LS
中科院分区：
文献类型：
--
作者：
Choi, WJ;Moon, HR;Jeong, LS
目标化合物17的制备和立体选择性合成（45-50%总收率）已由D-核糖完成。大体积保护基如TBDPS和三苯甲基增强了格氏反应过程中的面选择性，得到作为唯一产物的叔β-烯丙醇16，其以优异的产率氧化重排为关键分子17。
The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.