Issue 0, 1971

Preparation of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines

Abstract

A method for the synthesis of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines is described which involves as a key step the isomerisation of a 4-acyl- or 4-alkoxycarbonyl-1-[2-(indol-3-yl)ethyl]-1,2,3,6-tetra-hydropyridine to a 4-acyl- or 4-alkoxycarbonyl-1-[2-(indol-3-yl)ethyl]-1,2,3,4-tetrahydropyridine (not isolated). This, in turn, in reacting as a cyclic enamine, provides by protonation an electrophilic centre for closure on to the indole α-position. The 4-acyl-1-[2-(indol-3-yl)ethyl]-1,2,3,6-tetrahydropyridines can be cyclised in an alternative manner to give compounds comprising four of the five skeletal rings of the Iboga alkaloids.

Article information

Article type
Paper

J. Chem. Soc. C, 1971, 736-743

Preparation of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines

M. S. Allen, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1971, 736 DOI: 10.1039/J39710000736

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