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2136354 
Journal Article 
Synthesis of the dihydro diols and diol epoxides of chrysene from chrysene 
Fu, PP; Harvey, RG 
1979 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
HEEP/80/07605 
44 
22 
3778-3784 
WOS:A1979HS22800008 
HEEP COPYRIGHT: BIOL ABS. Synthesis of the 1,2- and 3,4-trans dihydro dioles (1a and 2a) of chrysene and the corresponding anti-isomeric diol epoxides (3a and 4) is described. Synthesis of both 1a and 2a is accomplished in only 7 steps from chrysene via initial hydrogenation over Adam's catalyst, dehydrogenation of the resulting 1,2,3,4-tetrahydrochrysene to a mixture (2:1) of 1,2- and 3,4-dihydrochrysene, Prevost reaction and chromatographic separation of isomers, followed by dehydrogenation and basic methanolysis of each isomer. An alternative regiospecific synthesis of 1a involving initial hydrogenation of chrysene over a PtO2-Pd 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 1a to exist preferentially in a diequatorial conformation, while 2a is exclusively diaxially oriented. Expodiation of 1a 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 phiX174 DNA viral replication in Escherichia coli spheroplasts.