Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: a formal total synthesis of lukianol A |
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Authors: | Liu J H Yang Q C Mak T C Wong H N |
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Institution: | Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China. |
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Abstract: | A combined use of alpha-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 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. |
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