Synthetic model of a new deoxybenzoin derivative from Deguelia hatschbachii A.M.G. Azevedo

• Autor(a) principal: Magalhães,A. F.
• Data de Publicação: 2005
• Outros Autores: Magalhães,E. G., Trazzi,G., Moraes,V. R. de S.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Eclética Química
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-46702005000100006
• topic: Deguelia hatschbachii; Leguminosae; deoxybenzoin

In this paper we describe the synthesis of 2´,4´-dimethoxy-8-(propyl-2-one)-deoxybenzoin, a new compound employed as a model for the comparison with the respective spectral data for 6',4-dihydroxy-3'-(3,3- dimethylallyl)-2",2"-dimethylchromene(5",6":5',4')-2'-methoxy-8-(propyl-2-one) deoxybenzoin, recently isolated from Deguelia hatschbachii A.M.G. Azevedo. Both compounds have a "propyl-2-one" group attached to C-8 of the deoxybenzoin skeleton, for which there is no precedent in the literature. The Friedel-Crafts reaction of 1,3-dimethoxybenzene with phenylacetyl chloride furnished 2´,4´-dimethoxydeoxybenzoin, that after reaction with allyl bromide gave 2´,4´-dimethoxy-8-(allyl)-deoxybenzoin . Wacker oxidation gave the desired model compound in 15% overall yield. The corresponding spectral data reinforced the structure previously determined for the natural product.