Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

Rafael Bautista; Alberto V. Jerezano; Joaquín Tamariz

doi:10.1055/s-0032-1317175

Synthesis, Table of Contents

Synthesis 2012; 44(21): 3327-3336
DOI: 10.1055/s-0032-1317175

paper

Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

Rafael Bautista

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, 11340 México, D.F., Mexico, Fax: +52(55)55866621 Email: jtamariz@woodward.encb.ipn.mx

,

Alberto V. Jerezano

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, 11340 México, D.F., Mexico, Fax: +52(55)55866621 Email: jtamariz@woodward.encb.ipn.mx

,

Joaquín Tamariz*

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, 11340 México, D.F., Mexico, Fax: +52(55)55866621 Email: jtamariz@woodward.encb.ipn.mx

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Abstract

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Abstract

An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

Key words

1-methoxycarbazoles - α-ketoenamines - palladium(II) - cyclization - glycozolicine

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References

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