Total Synthesis of Dihydrocinchonamine

Cinchonamine (1) is the best known member of a small group of 2,2-indolquinuclidine alkaloids found in the bark of certain Cinchona and Remijia species 1 and in the leaves of Isertia hypoleuca 2 . Its isolationwas reported in 1881 3 , the ambiguities was elucidated in 1950 4 , and very recently 5 th ambiguities concerning the absolute configuration at C-3 were resolved. Synthetic efforts resulted in the partial synthesis of cinchonamine 6 , dihydrocinchonamine 7,8 , and its 10-methoxy-analog 5,9 from cinchonine, cinchonidine and quinine.