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Synthesis of Aristotelia-type alkaloids. Part V. Biomimetic synthesis of (±)-aristomakine and (±)-aristomakinine

✍ Scribed by Stefan Burkard; Hans-Jürg Borsehberg

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
282 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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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