On-line version ISSN 1678-4618
MAGALHAES, A. F.; MAGALHAES, E. G.; TRAZZI, G. and MORAES, V. R. de S.. Synthetic model of a new deoxybenzoin derivative from Deguelia hatschbachii A.M.G. Azevedo. Eclet. Quím. [online]. 2005, vol.30, n.1, pp.43-49. ISSN 1678-4618. http://dx.doi.org/10.1590/S0100-46702005000100006.
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.
Keywords : Deguelia hatschbachii; Leguminosae; deoxybenzoin.