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Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids
Science China Chemistry ( IF 10.4 ) Pub Date : 2019-09-26 , DOI: 10.1007/s11426-019-9598-1
Sankar Rao Suravarapu , Bettina Peter , Philippe Renaud

A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed. The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines. By using complementary strategies, these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5) and their conversion to a variety of indolizidine alkaloids such as coniceine, indolizidine 209D and 167B, 5-epi-indolizidine 249A and monomorine has been reported in the literature.



中文翻译:

自由基介导的2-乙烯基吡咯烷衍生物的加氢烷基化:吲哚并立生物碱的多用途进入

已经开发了制备两种简单的光学纯的吲哚利兹-5-酮的简捷方法。使用Boc保护的2-乙烯基吡咯烷的三乙基硼烷/邻苯二酚介导的加氢烷基化作用实现了关键链的延长过程。通过使用互补策略,可以在完全控制C(5)的立体化学的情况下将这两个双环内酰胺烷基化,并将其转化为多种吲哚并立生物碱,例如康乃馨,吲哚并立定209D和167B,5-表位-吲哚并立定249A,单mor有文献报道。

更新日期:2019-09-26
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