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

DOI: 10.1590/S0100-46702005000100006

Keywords: deguelia hatschbachii, leguminosae, deoxybenzoin.

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Abstract:

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.

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