Total synthesis of new indolo[2,3-a]quinolizine alkaloids sempervirine type, potential pharmaceuticals

Add time:09/30/2019    Source:infona.pl

Total synthesis of the two series of new pentacycilc cycloalk[g]Indolo[2,3-a]quinolizine (cas 239-15-6) alkaloids (modified sempervirine possessing the wide range of activity), has been elaborated in five steps from 5-acetyl-3-methylthio-1,2,4-triazine (obtained from the simple acyclic materials). In the two key steps: inverse electron demand Diels–Alder reaction of precursor with cyclic enamines and the following Fischer indolization of 3-acetyl-1-methylthiocycloalka[c]pyridines, the AB–DE synthons, has been obtained. The final stages: desulfuration, and formation of the C-ring via the Gribble method have led to the expected zwitterionic alkaloids. Model syntheses of the indolopyridocoline and its methoxy analogue from 2-acetylpyridine have been performed for investigation of the microwave-induced Fischer synthesis of sensitive indoles and for obtaining compounds for comparative study of spectroscopic data.

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