Synthesis of the Diol Epoxide Metabolites of Carcinogenic PAH

Abstract

The active metabolites of alternant carcinogenic polycyclic aromatic hydrocarbons (PAH) with 4-5 fused rings are now readily available through synthesis. Development of new synthetic methodologies that are more efficient and are also applicable to larger PAH and to nonalternant PAH will be discussed. Syntheses of the unusual diol epoxide metabolites of the methylene-bridged PAH 4H-cyclopenta[def]chrysene, in both unsubstituted and substituted bay regions will be described. The latter is the first example of diol epoxide in which the epoxide function is located in an alkyl-substituted bay region site. Syntheses will also be outlined of the large polyarene benzo[s]picene, and its fjord region dihydrodiol and diol epoxide metabolites via a novel route.

Key Words:

• 4H-Cyclopenta[def]chrysene
• benzo[s]picene
• diol epoxide