Stereoselective Synthesis and Reactions of a Diol-Epoxide Derived from Benzo[a]pyrene

  • Donald M. Jerina
  • Haruhiko Yagi
  • Oscar Hernandez


In the course of examining the metabolism-induced binding of benzo[a]pyrene (BP) to DNA in the presence of active liver microsomes, Borgen et al. (1) made the intriguing observation that further metabolism of trans-7,8-dihydroxy-7,8-dihydro-BP resulted in much more extensive binding to DNA than that observed with two other metabolic dihydrodiols or with BP itself. Subsequently, Sims et al. (2) suggested that the facile binding of this dihydrodiol was mediated by formation of an oxide at the 9,10-double bond. Synthesis of the suspected binding agent, 7,8-dihydroxy-9,10-epoxy,7,8,9,10-tetrahydro-BP, was claimed to result from the action of m-chloroperoxybenzoic acid on the parent dihydrodiol (2). We have considered the possibility that the suspected high chemical reactivity of this diol-epoxide from BP might well be due to anchimeric assistance (3,4) by the neighboring hydroxyl group at C-7.


Oxirane Ring Stereoselective Synthesis Polycyclic Hydrocarbon Silyl Ether Transition State Geometry 
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Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • Donald M. Jerina
    • 1
  • Haruhiko Yagi
    • 1
  • Oscar Hernandez
    • 1
  1. 1.National Institute of Arthritis, Metabolism, and Digestive DiseasesNational Institutes of HealthBethesdaUSA

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