Abstract

GUZMAN, José Agustín et al. Estudio Sintético de Furanoeremofilanos: Síntesis de la 13-Nor-9-oxoeuryopsina. Rev. Soc. Quím. Méx [online]. 2004, vol.48, n.4, pp.250-255. ISSN 0583-7693.

In this paper we describe a strategy designed for the synthesis of the basic skeleton of furanoeremophilanes, the most abundant class of furanosesquiterpenes. The key steps in the synthetic scheme involve a regio- and stereoselective double alkylation of an enone (tandem vicinal difunctionalization) and construction of the central ring via an intramolecular electrophilic aromatic substitution. To demonstrate this approach, we synthesized the norfuranoeremophilane 1 in 8 steps, starting from 2-methyl-2-cyclohexenone and 3-furaldehyde.

Keywords : Furanoeremophilane synthesis; 13-nor-9-oxoeuryopsin; tandem vicinal difunctionalization.

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