Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A

Article abstract of DOI:10.1021/jo9915224

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.