129099-68-9Relevant academic research and scientific papers
Synthesis of Aristotelia-Type Alkaloids
Burkard, Stefan,Borschberg, Hans-Juerg
, p. 298 - 302 (1990)
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.
