Regiocontrolled synthesis of enantiopure 3,3'-thiosubstituted biphenyls |
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Authors: | Capozzi Giuseppe Delogu Giovanna Fabbri Davide Marini Manuela Menichetti Stefano Nativi Cristina |
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Institution: | Centro CNR "Chimica dei Composti Eterociclici", Dipartimento di Chimica Organica, Universita' di Firenze, via G. Capponi 9, I-50121, Firenze, Italy. |
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Abstract: | Sulfenylation of 6,6'-dimethoxy-2,2'-dihydroxybiphenyl, used as a racemic mixture and single enantiomers, by phthalimidesulfenyl chloride afforded the corresponding 3,3'-N,N'-dithiophthalimide with complete regioselectivity. Simple manipulations of the latter compound allowed access to the corresponding bis-thiol or o-thioquinone as useful intermediates for the synthesis of new sulfur-containing open-chain and macrocyclic C(2) enantiopure ligands. The application of this methodology to the preparation of a biphenyl bearing two cysteine units as potential HIV-1 protease inhibitor is also described. |
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