Stereoselective Synthesis of Putative Diol Epoxide Metabolites of 4H-Cyclopentachrysene

Article abstract of DOI:10.1021/jo00120a039

Synthesis of the anti-diol epoxide derivatives of the methylene-bridged polycyclic aromatic hydrocarbon 4H-cyclopentachrysene in both the bridge- and non-bridge-substituted rings (2 and 3) and the syn-diol epoxide derivative in the non-bridge-substituted ring (14) are described.These compounds are suspected to be active carcinogenic metabolites of the parent hydrocarbon.They are the first examples of the diol epoxide derivatives of a nonalternant methylene-bridged tumorigenic hydrocarbon to be synthesized.The bridge-substituted anti-diol epoxide derivative 2 is relatively stable, despite its relatively strained structure, and it possesses a unique "locked" structure which severely restricts conformational interconversion.