ALSTONIA ALKALOIDS. I. DEGRADATION OF ALSTONINE TO β-CARBOLINE BASES AND THE REDUCTION OF TETRAHYDROALSTONINE WITH SODIUM AND BUTYL ALCOHOL

The Journal of Organic Chemistry
1942.0

Abstract

1. The formula of alstonine has been definitely checked as C21H20N2O8. 2. From the products of alkali fusion of alstonine and tetrahydroalstonine, barman, norharman, indole-α-carboxylic acid, and three bases of undetermined structure, probably β-carboline derivatives, have been obtained. 3. Thermal decomposition of alstonine leads to the formation of three bases of undetermined structure, but which are apparently β-carboline derivatives. 4. Reduction of tetrahydroalstonine with sodium and butyl alcohol leads to a new base, hexahydroalstonol, C20H26N2O2, the absorption curve for which is identical with that of yohimbine and α,β-dimethylindole. 5. 1-Ethyl-3-carboline and 3-ethyl-β-isocarboline have been prepared. 6. A partial structure for alstonine is discussed. © 1942, American Chemical Society. All rights reserved.

Knowledge Graph

Similar Paper