Two natural products 1,3-bis(2-hydroxy-4-methoxyphenyl)propane (1) and 1,3-bis(2,4-dihydr- oxyphenyl)propane (2), isolated from the dried rhizomes of Dioscorea composita Hemsl., were first synthesized by acylation, methoxymethyl protection or methylation, condensation, catalytic hydrogenation, deoxygenation and deprotection starting from resorcinol. 2,4-Dihydroxybenzaldehyde and 2,4-dihydroxyacetophenone were synthesized from resorcinol, which were followed by protection with standard methylation or methoxymethylation to afford 4-methoxy-2-methoxymethoxybenzaldehyde and 2-hydroxy-4-methoxyl- acetophenone. The desired chal-cone was obtained by condensing 4-methoxy- 2-methoxymethoxyben- zaldehyde with 2-hydroxy-4-methoxylacetophenone, which was then reducted by catalytic hydrogenation and deoxygena-tion to give the title compound 1,3-bis(2-hydroxy- 4-methoxyphenyl)propane (1). Another desired product 1,3-bis(2,4-dihydroxyphenyl)propane (2) was obtained by treatment of 1 with boron tribromide in anhydrous methylene dichloride. Their structures were confirmed by ¹H NMR, IR and MS techniques.

Key words: chalcone, natural product, synthesis, 1,3-diarylpropane