Dihydrocinchonamine

The Alkaloids: Chemistry and Physiology Volume 11, 1968, Pages 73–77

Chapter 3 The 2,2′-Indolylquinuclidine Alkaloids[Reference: WebLink]

The group of 2,2′-indolylquinuclidine alkaloids has a narrow distribution and only two members have been discovered in the past few years. This chapter focuses on accepted stereochemistry, although an unequivocal proof is still required for C-3 in cinchonamine.
METHODS AND RESULTS:
The course of the acetylation of cinchonamine has been restudied using the parent base, Dihydrocinchonamine and O-tritylcinchonamine. Many of the compounds formed in this investigation were amorphous, but were satisfactorily characterized via thin-layer chromatography and mass spectrometry, along with UV- and IR-measurements. At low temperatures (dry ice-acetone), cinchonamine yields O-acetylcinchonamine. Dihydrocinchonamine behaves analogously upon treatment with acetic anhydride, although there are difficulties because of the amorphous nature of the products.
CONCLUSIONS:
Cinchophyllamine contains two 5-methoxyindole nuclei with unsubstituted nitrogen atoms, a vinyl group, and two basic nitrogens of which one is tertiary and the other secondary. A reinvestigation of the alkaloid content of the leaves of Cinchona legeriana Moens gives, besides quinamine, two new bases analyzing for C31H36N4O2—cinchophyllamine and isocinchophyllamine.