F. Bracher et D. Hildebrand, BETA-CARBOLINE ALKALOIDS .4. SYNTHESES OF 1-ALKYL-BETA-CARBOLINES ANDSTRUCTURE REVISION OF LYCII ALKALOID-I, Liebigs Annalen der Chemie, (12), 1993, pp. 1335-1337
Palladium-catalyzed coupling reactions of 1-chloro-beta-carboline (1)
with triethylborane and trimethylaluminum give the alkaloids 1-ethyl-b
eta-carboline (2) and harman (5). The intermediate 4 on treatment with
ethyl formiate gives 9-formylharman (6). Comparison of the spectrosco
pic data shows, that lycii alkaloid I does not have the structure 6, b
ut is identical with the alkaloid 1-acetyl-beta-carboline (7).