Journal of the Chemical Society. Perkin transactions I p. 3168 - 3175 (1981)
Update date:2022-08-10
Topics:
Kametani, Tetsuji
Kanaya, Naoaki
Hino, Hiroaki
Huang, Shyh-Pyng
Ihara, Masataka
Enamine annulation between 3,4-dihydro-1-methyl-β-carboline (4) and dimethyl 3-methoxyallylidenemalonate (5) yielded 2-(2,2-dimethoxyethyl)-2,3,4,6,7,12-hexahydro-3-methoxycarbonyl-4-oxoindolo<2,3-a>quinolizine (6), which was transformed into (+/-)-dihydrocorynantheol (1). (+/-)-Corynantheal (19), which is convertible into (+/-)-corynantheine (2) and (+/-)-ajmalicine (3), was stereoselectively synthesised from (6) via epimerisations at the angular position using Adams catalyst.
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