Abstract
A new short synthesis of the indole alkaloid eburnamonine (1), starting from the easily available enamine (3) (1,12b-didehydroindolo[2,3-a]quinolizidine) is described. Pentacyclic lactam (7) (18-nor-19- ethoxycarbonyl-21-epieburnamonine) (trans D/E ring juncture), the key intermediate in this synthesis, was prepared from enamine (3) by dialkylating with ethyl iodoacetate in the presence of diisopropylethylamine (DIPEA). LiAlH 4 -reduction of lactam (7) gave a 2:1 mixture of compounds (10a) (21-epi-18-hydroxyeburnamine) and (10b) (16-epi-21-epi-18-hydroxyeburnamine)
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