"Síntese e confirmação estrutural de 1,3-Diarilpropanos naturais"

Abstract

This work describes the synthesis of four 1,3-Diarylpropanes: 1-(4'- hidroxy-5'-methyl-2'methoxyphenyl)-3-(2"-hidroxy-4",5"-methylenedioxyphenyl)- propane (IX-B) was synthesized with the purpose of confirming the proposed structures for the natural 1,3-diarylpropane extracted from Iryanthera laevis ; 1-(4'- hydroxy-2'-methoxyphenyl)-3-(4"-hydroxyphenyl)-propane (XV) (Broussonin B) and 1-(2'-hydroxy-4'-methoxyphenyl)-3-(4"-hydrixyphenyl)-propane (XlV) (Broussonin A) are phytoalexins isolated from Broussonetia papyrifera Vent., which show antifungic and antibacterian activities; 1-(2',4'-dimethoxyphenyl)-3-(4"-hydroxyphenyl)-propane (XVlII) is a synthetic product prepared by catalytic hydrogenation of 4-benzyloxy-2',4'- dimethoxychalcone. The synthetic pathway employed in this work involved the preparation of substituted acetophenones and benzaldehydes which, by aldol condensation, afforded the corresponding chalcones. These were submitted to catalytic hidrogenation (Pd-C 10%) and were characterized by I.R, Mass Spectrometry and MNR (1H, 13C, COSY & HETCOSY).