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Paper | Regular issue | Vol 57, No. 2, 2002, pp.259-267
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9388
A Concise Synthesis of the Natural Carbazole Mukonine

Alejandra Zempoalteca and Joaquín Tamariz*

*Departamento de Químíca Orgánica, Escuela Nacional de Ciencias Biológicas, I. P. N., Prol. Carpio y Plan de Ayala S/N,11340, Mexico, D.F.

Abstract

A short and total synthesis of the natural carbazole mukonine (1) is described, based on a regioselective Diels-Alder reaction of N-phenyl 4,5-dimethylidene-2-oxazolidinone (9) with methyl propiolate (10). Successive transformation of the cycloadduct in one step to the corresponding phenylarylamine (16), and palladium promoted cyclization of the latter provided carbazole (1).