Journal of Organic Chemistry p. 3587 - 3595 (2000)
Update date:2022-08-02
Topics:
Liu, Jian-Hui
Yang, Qing-Chuan
Mak, Thomas C. W.
Wong, Henry N. C.
A combined use of α-lithiation and nucleophilic substitutions of N,N- dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the β-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.
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Doi:10.1246/cl.2000.646
(2000)Doi:10.1093/oxfordjournals.jbchem.a132246
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(2001)Doi:10.1016/S0957-4166(00)00106-3
(2000)Doi:10.1007/BF02252007
(1999)Doi:10.1016/S0960-894X(00)00182-7
(2000)