The first synthesis of three naturally occurring phenylpropanoids, boropinol A (1), boropinal C (2) and boropinic acid (3), is described. The reaction of vaniline (4) with prenyl bromide in DMF gave the 0- prenylated product 5 in 84% yield. Condensation of 5 with Ph-3P= CHCO- 2Et in DME produced ester 6 in 52% yield. Hydrolysis of 6 with aqueous KOH followed by acidification gave boropinic acid (3) in 91% yield. Compound 3 was obtained as a nice crystal instead of a liquid as that reported in literature. The structure of 3 was confirmed by X-ray crystal structural analysis in addition to its solution spectrum data. Reduction of 3 by LiAlHj in dry diethyl ether gave a mixture of compound 1 and 7. This mixture was not seperated and was oxidized by K- 2Cr-2O-7 in DMSO to give compound 2 in 61% yield. Pure boropinol A (1) was obtained in 70% yield by the reduction of 2 with NaBHi in CH-3OH.

Key words: vanillin, 1HNMR, IR, XRD, CRYSTAL STRUCTURE, MOLECULAR STRUCTURE