Journal of the American Chemical Society p. 9139 - 9150 (1995)
Update date:2022-08-03
Topics:
L?gers, Michael
Overman, Larry E.
Welmaker, Gregory S.
A concise enantioselective total synthesis of the cardiovascular agent (-)-ajmalicine and an approach toward the synthesis of (+)-19-epiajmalicine are described. The key step of the (-)-ajmalicine synthesis is a carboxylate-terminated N-acyliminium ion biscyclization (74 → 67), which assembles the D and E rings of this heteroyohimbine alkaloid in one step. A related carboxylate-terminated iminium ion biscyclization (28 → 29) is the central step in the approach to (+)-epiajmalicine.
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