Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles:: A formal total synthesis of lukianol A
Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles:: A formal total synthesis of lukianol A
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DOI：
10.1021/jo9915224
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发表时间：
2000-06-16
影响因子：
3.6
通讯作者：
Wong, HNC
中科院分区：
文献类型：
--
作者：
Liu, JH;Yang, QC;Wong, HNC
N，N-二甲基3，4-双（三甲基甲硅烷基）LH-吡咯-1-磺酰胺8 c的α-锂化和亲核取代的组合使用导致几种2-取代的3，4-双（三甲基甲硅烷基）-1H-吡咯-1-磺酰胺。利用三甲基硅基的β-效应，实现了2，3，4-三取代1H-吡咯23和34的高度区域选择性合成。利用该方法制备了海洋天然产物lukianol A（3）。
A combined use of alpha-lithiation and nucleophilic substitutions of N,N-dimethyl 3,4-bis(trimethylsilyl)LH-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the beta-effect of a trimethylsilyl group, a highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles 23 and 34 was accomplished. The marine natural product lukianol A (3) was prepared utilizing this strategy.