Synthesis of Dihydrodiol Metabolites of Naphtho[8,1,2- GHI ]Chrysene and Dibenzo[ C,MNO ]Chrysene

Syntheses of naphtho8,1,2- ghi ]chrysene (naphtho1,2- e ]pyrene, N e ]P) 1 , dibenzo c,mno ]chrysene (naphtho1,2- a ]pyrene, N a ]P) 2 and their dihydrodiol metabolites are described. The hydrocarbons N e ]P 1 and N a ]P 2 and their fjord region dihydrodiols 12 and 19 were synthesized using a Suzuki cross-coupling reaction followed by the appropriate manipulation of the functional groups. The K-region cis dihydrodiols of N e ]P-4,5-diol 20 , N a ]P-4,5-diol 23 , N a ]P-7,8-diol 24 were obtained by OsO 4 oxidation. The cis diols thus obtained were first converted to the corresponding quinones with pyridinium chlorochromate and, finally, to the desired trans dihydrodiols 22 , 27 , and 28 by NaBH 4 reduction. The mixture of trans N a ]P-4,5- and 7,8-dihydrodiols was separated by high-performance liquid chromatography.