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Synthesis 2011(6): 929-933  
DOI: 10.1055/s-0030-1258444
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of the Natural Carbazoles Glycozolicine, Mukoline, and Mukolidine, Starting from 4,5-Dimethyleneoxazolidin-2-ones

Rafael Bautistaa, Pablo Bernala,b, Luisa E. Montiela, Francisco Delgadoa, Joaquín Tamariz*a
a 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)57296300/46211; e-Mail: jtamariz@woodward.encb.ipn.mx;
b Departamento de Investigación y Desarrollo, Signa, S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50200 Toluca, Edo. de México, Mexico
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Publikationsverlauf

Received 19 November 2010
Publikationsdatum:
18. Februar 2011 (online)

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Abstract

A novel and efficient synthesis of naturally occurring 1-methoxycarbazoles glycozolicine, mukolidine, and mukoline is developed by applying a regioselective Diels-Alder reaction of a 4,5-dimethyleneoxazolidin-2-one with acrolein. The cycloadduct is transformed to the corresponding functionalized diarylamine. The key palladium-catalyzed cyclization/deformylation cascade reaction of the latter leads to glycozolicine in high overall yield. Oxidation of the C6 methyl group provides the 6-formylcarbazole mukolidine, which is reduced to the respective natural alcohol mukoline.

Key words

1-methoxycarbazoles - 4,5-dimethyleneoxazolidin-2-one - glycozolicine - mukolidine - mukoline - palladium(II) cyclization - decarbonylation

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