Studies On The Total Synthesis Of Rutecarpine-type Alkaloids

This thesis focuses on the total synthesis of rutecarpine-type indole Alkaloids, which is divied into two parts. Part one studies on the syntesis of 2-methoxy rutecarpine, Orisuaveoline A and Orisuaveoline B.Rutecarpine-type indole alkaloids, one kinds of alkaloids with indoloquinazolin-type skeleton, have various important biological activities.One of the key starting intermediates——2-amino-4-methoxybenzolic acid (24) was prepared in 5 steps transformations starting from 4-methylanaline. Compound 7, another synthesis fragment was accomplished by cyclization of tryptamine with bis-trichloromethyl carbonate. The first total synthesis of 2-methoxyrutecarpine (2) was achieved by condensated-cyclization of compounds 24 and 7 in toluene.Another synthetic approach was focused on the preparation of key intermediate——compound 12.Starting from commercially available material piperonal, compound 12 was accomplished by Henry condensation, nitrification, Hemetsberger reaction, reductive aminoation and subsequent replacement with KCN.The further research works is in progress now.Parts two reviews on the total synthetic progress of some alkaloids which have indole-type skeleton with important biological activities.38 references are cited therein.