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

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Abstract

The preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyls (aR)-(+)-1 and (aS)-(-)-1 were obtained by the corresponding menthylcarbonate diastereomer and successive reduction. The absolute configuration and specific 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 enantiomers of 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for the enantiomer (aS)-(-)-1. © 2007 Elsevier Ltd. All rights reserved.

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Fabbri, D., Dettori, M. A., Delogu, G., Forni, A., Casalone, G., Palmieri, G., … Rozzo, C. (2007). 2,2′-Dihydroxy-3,3′-dimethoxy-5,5′-dimethyl-6,6′-dibromo-1,1′-biphenyl: preparation, resolution, structure and biological activity. Tetrahedron Asymmetry, 18(3), 414–423. https://doi.org/10.1016/j.tetasy.2007.01.017

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