Development and application of catalytic multi-component coupling and ring-forming reactions

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To develop practical synthetic method of polycyclic heterocycles such as tetrahydroisoquinolines and oxindoles, which are very important as biologically active drug-templates, several metal-catalyzed reactions of 2-alkynylbenzylamines and carbamoyl chlorides bearing an alkene or diene moiety were investigated with In(OTf)_3, AuCl・PPh3/AgNTf_2, and Pd(dba)_2. Consequently, we have succeeded in the formal synthesis of epieburnamonine and isoelacomine as well as the construction of the core structures of ecteinascidin 743 and vincorine.