ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730209
