Syntheses of Bioactive Compounds using Functional Carbanions

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Functional carbanions, such as ynolates and gem-dianions, and their new reactions were developed, and bioactive compounds were synthesizedvia these new reactions. Total synthesis stemonamine, one of contents of traditional Chinese medicine, Stemona japonica, was achieved by using the tandemreaction initiated by ynoaltes. New reactive species, gem-dianions, were generated by double lithiation of dibromoamides. Using the dianions, tandem aromatic substitution-electrocyclic reaction affording benzoisoqunoline was developed. An -heteroatom effect of olefination with ynoaltes revealed the high reactivity of -alkoxy esters towards olefination. Using a flow microreactor, ynolates could beprepared at ambient temperature