Efficient Total Synthesis of Racemic Bisabolane Sesquiterpenes Curcuphenol and Xanthorrhizol Starting from Substituted Acetophenones

Authors

  • Luisa E. Montiel,

    1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, D. F. Mexico, (phone/fax: +52-55-57296300/46211)
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  • L. Gerardo Zepeda,

    1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, D. F. Mexico, (phone/fax: +52-55-57296300/46211)
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  • Joaquín Tamariz

    1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, D. F. Mexico, (phone/fax: +52-55-57296300/46211)
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Abstract

A total synthesis of natural bisabolane sesquiterpenes curcuphenol (1) and xanthorrhizol (2) was developed by using the substituted acetophenones 4 and 5, respectively, as starting materials. The acetyl group of the latter was activated through ethoxycarbonylation to carry out the prenylation, which was performed successfully to give their respective precursors 11a and 11b, and 21 that were converted into the corresponding natural sesquiterpenes 1 and 2, respectively, over four steps and in high overall yields.

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