SYNTHESIS OF THE DIHYDRO DIOLS AND DIOL EPOXIDES OF CHRYSENE FROM CHRYSENE

Synthesis of the 1, 2- and 3, 4-trans dihydro diols (la and 2a) of chrysene and the corresponding anti isomeric diol epoxides (3a and 4) is described. Synthesis of both la and 2a is accomplished in only seven steps from chrysene via initial hydrogenation over Adam's catalyst, dehydrogenation of the resulting 1, 2, 3, 4-tetrahydrochrysene by NBS and DBN to a mixture (2:1) of 1, 2- and 3, 4-dihydrochrysene, Prévost reaction and chromatographic separation of isomers, followed by dehydrogenation and basic methanolysis of each isomer. An alternative regiospecific synthesis of la involving initial hydrogenation of chrysene over a Pt02-Pd/C catalyst to 1, 2, 3, 4, 5, 6-hexahydrochrysene is also presented. These methods offer major advantages over established methods for the synthesis of polyarene dihydro diols which entail more complex multistep ring construction. NMR analysis indicates la to exist preferentially in a diequatorial conformation, while 2a is exclusively diaxially oriented. Epoxidation of la affords stereospecifically the anti diol epoxide 3a, whereas similar reaction of 2a furnishes the corresponding anti and syn diol epoxides in a 5:3 ratio. Preliminary experiments indicate 3a to be a potent inhibitor of the infectivity of ØX174 DNA viral replication in E. coli spheroplasts, while 4 appears only weakly active. © 1979, American Chemical Society. All rights reserved.