Helvetica Chimica Acta p. 298 - 302 (1990)
Update date:2022-08-02
Topics:
Burkard, Stefan
Borschberg, Hans-Juerg
Biomimetic syntheses of racemic aristomakinine ((+/-)-3) and aristomakine ((+/-)-4), an unusual indole alkaloid bearing an N-isopropyl group, are described.The key step is a Grob-type fragmentation of anti-15-aristotelinyl methanesulfonate ((+/-)-2) to the intermediate iminium ion I which, upon subsequent hydrolysis, furnished aristomakinine ((+/-)-3).On the other hand, the same intermediate could be reduced in situ to aristomakine ((+/-)-4).The controversial relative configurations of the two alkaloids have been firmly established by means of NOE difference experiments.
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