As. Kiselyov et al., EFFICIENT SYNTHESES OF THE ANTI-DIOL AND SYN-DIOL EPOXIDE METABOLITESOF THE CARCINOGENIC POLYCYCLIC AROMATIC HYDROCARBON BENZO[G]CHRYSENE, Journal of organic chemistry, 60(19), 1995, pp. 6123-6128
Two new synthetic approaches to the active fjord region anti- and syn-
diol epoxide metabolites (3a and 3b) of the potent carcinogenic hydroc
arbon benzo[g]chrysene are described. The first of these methods entai
ls initial synthesis of the key intermediate 12-hydroxybenzo[g]chrysen
e which is transformed in two steps to ans-11,12-dihydroxy-11,12-dihyd
robenzo[g]chrysene, the synthetic precursor of 3a and 3b. The second m
ethod involves in the key step oxidative photocyclization of a 1,2 dia
rylethylene having methoxy groups at appropriate sites for subsequent
conversion to the dihydrodiol function. These methods allow efficient
preparative scale synthesis of the benzo[g]chrysene diol epoxides requ
ired as starting compounds for the synthesis of specifically alkylated
benzo[g]chrysene-oligonucleotide adducts needed for site-directed mut
agenesis and other studies to elucidate molecular mechanisms of carcin
ogenesis.