The asymmetric synthesis of the [D-8]-labeled (-)-(S)-dihydroxyverbacine, the terminal precursor in the biogenesis of the macrobicyclic spermine alkaloids aphelandrine and orantine
L. Nezbedova et al., The asymmetric synthesis of the [D-8]-labeled (-)-(S)-dihydroxyverbacine, the terminal precursor in the biogenesis of the macrobicyclic spermine alkaloids aphelandrine and orantine, HELV CHIM A, 83(11), 2000, pp. 2953-2960
The asymmetric synthesis of the unlabeled and [D-8]-labeled terminal precur
sors, 4 ((-)-(S)-dihydroxyverbacine) and 19, respectively, in the biogenesi
s of the spermine alkaloids aphelandrine (5) and orantine (6), respectively
, is described. A partial synthesis of the alkaloid (-)-(S)-[(E)-4-methoxyc
innamoyl]buchnerine (10) is also presented.