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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 1
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Original Articles

Total Synthesis of Dihydrocinchonamine

, &
Pages 55-61 | Received 05 Jan 1972, Published online: 03 Jan 2007
 

Abstract

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 hypoleuca2. Its isolationwas reported in 18813, the ambiguities was elucidated in 19504, and very recently5 th ambiguities concerning the absolute configuration at C-3 were resolved. Synthetic efforts resulted in the partial synthesis of

cinchonamine6, dihydrocinchonamine7,8, and its 10-methoxy-analog5,9 from cinchonine, cinchonidine and quinine.

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