Synthesis of Potential Metaboliters in the 1,2,3,4, and 5,6,7,8 Benzo Ring Positions of the Polycyclic Aromatic Hydrocarbon Benzo(G)Chrysene.
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH
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Polycyclic aromatic hydrocarbons PAH are unavoidable pollutants of our environment. Studies have linked cancers directly to contact with these contaminants. Within the past ten years evidence supports the finding that the ultimate carcinogen in the metabolic chain of a PAH is the bay region diol epoxide. The most studied PAH is bensoapyrene. Recent tests indicate benzogchrysene XL, another PAH, is also a potent carcenogen. Research efforts in this dissertation involve the synthesis of potential metabolites of this PAH. Because XL has two fjord and three bay region benzylic positions, it will permit assessment of steric factors associated with biological activity. Recent publications include vicinal hydroxyl orientation effects in their structure reactivity discussions. This dissertation describes the total synthese of or - -3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzogchrysene isomers 1 and 2. It also includes synthesis of the 1,2-dihydroxy and 3,4-dihydro-3-4-dihydorxy derivatives. Syntheses associated with the 5,6,7,8 benzo ring include 7,8-dihydro 5,6-dihydro--5,6-dihydroxy and 5,6,7,8-tetrahydro-5,6-epoxide. A synthesis of the parent PAH, benzogchyrsene is also included.
- Organic Chemistry