Synthesis and structural confirmation of natural 1,3-diarylpropanes

1-(4’-Hydroxy-5’-methyl-2’-methoxyphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl) propane (7), 1,3-diarylpropane isolated from Iryanthera laevis, 1-(4’-hydroxy-2’-methoxyphenyl)-3-(4"-hydroxyphenyl)propane (2, broussonin B) and 1-(2’-hydroxy-4’-methoxyphenyl)-3-(4"-hydroxyphenyl)propane (1, broussonin A), isolated from Broussonetia papyrifera Vent. (Moraceae), and 1-(2’,4’-dimethoxyphenyl)-3-(4"-hydroxyphenyl)propane, a synthetic product prepared by catalytic hydrogenation of 4-O-benzyl-2’,4’-dimethoxychalcone, were synthesized. The synthetic pathway employed in this work involved the catalytic hydrogenation of chalcones obtained by base condensation of acetophenones and benzaldehydes.1-(4’-Hidroxi-5’-metil-2’-metoxifenil)-3-(2"-hidroxi-4",5"-metileno-dioxifenil)propano (7), 1,3-diarilpropano isolado de Iryanthera laevis (Myristicaceae), 1-(4’-hidroxi-2’-metoxifenil)-3-(4"-hidroxifenil)propano (2, broussonina B) e 1-(2’-hidroxi-4’-metoxifenil)-3-(4"-hidroxifenil) propano (1, broussonina A), isolados de Broussonetia papyrifera Vent. (Moraceae), e 1-(2’,4’-dimetoxifenil)-3-(4"-hidroxifenil)propano (4), um produto sintético oriundo da hidrogenação catalítica da 4-O-benzil-2’,4’-dimetoxichalcona, foram sintetizados. A rota sintética utilizada envolveu hidrogenação catalítica (Pd-C 10%) de chalconas obtidas por condensação aldólica de acetofenonas e benzaldeídos adequadamente substituídos