Constructions of tetrahydro-γ-carboline skeletons via intramolecular oxidative carbon–carbon bond formation of enamines?

Organic & Biomolecular Chemistry Pub Date: 2013-02-05 DOI: 10.1039/C3OB00039G

Abstract

The synthetically and biologically important 4-methyl and 4-methoxy tetrahydro-γ-carboline compounds were readily synthesized in high yields from an aryl amine and a 5-amino-3-oxopentanoate derivative through a series of reactions of enamination, oxidative annulation, deprotection/lactamization and the final reduction reaction of the carbonyl group. The underpinning strategy involves the oxidative C(sp2)–C(sp2) bond formation realized by either Pd(OAc)2/Cu(OAc)2 or a hypervalent iodine reagent.

Graphical abstract: Constructions of tetrahydro-γ-carboline skeletons via intramolecular oxidative carbon–carbon bond formation of enamines
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