2,2-dihydroxy-3,3-dimethoxy-5,5-dimethyl-6,6-dibromo-1,1-biphenyl: preparation, resolution, structure and biological activity.

Preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyl (aR)-(+)-1 and (aS)-(-)-1 were achieved respectively by the corresponding menthylcarbonate diastereomer and successive reduction. Absolute configuration and optical rotation were correlated by X-ray analysis of the crystal structure of diastereopure menthylcarbonate (aS,1R,1’R,2S,2’S,5R,5’R)-(-)-16. Preliminary biological evaluation of both racemic and enantiomers 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for enantiomer (aS)-(-)-1 .