Regiocontrolled synthesis of enantiopure 3,3'-thiosubstituted biphenyls.
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.
Capozzi
Giuseppe
G
Centro CNR "Chimica dei Composti Eterociclici", Dipartimento di Chimica Organica, Universita' di Firenze, via G. Capponi 9, I-50121, Firenze, Italy.
Delogu
Giovanna
G
Fabbri
Davide
D
Marini
Manuela
M
Menichetti
Stefano
S
Nativi
Cristina
C