Abstract
The mixture of pentacyclic intermediates ( 4) was successfully converted into the pharmacologically interesting indole alkaloid (±)-tacamine ( 1). In a similar manner, the two unnatural isomers of 1, (±)-14-epitacamine ( 9) and (±)-14-epi-16-epitacamine ( 10), were obtained from intermediate 7. The key reaction, an acid-catalyzed displacement of the dimethylamino group with the hydroxyl group, is believed to take place via an iminium intermediate.
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