Synthesis of dihydrodiol metabolites of naphtho[8,1,2-ghi]chrysene and dibenzo[c,mno]chrysene

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Abstract

Syntheses of naphtho[8,1,2-ghi]chrysene (naphtho[1,2-e]pyrene, N[e]P) 1, dibenzo[c,mno]chrysene (naphtho[1,2-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 OsO4 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 NaBH4 reduction. The mixture of trans N[a]P-4 5- and 7,8-dihydrodiols was separated by high-performance liquid chromatography.

Original languageEnglish (US)
Pages (from-to)297-305
Number of pages9
JournalPolycyclic Aromatic Compounds
Volume23
Issue number3
DOIs
Publication statusPublished - Aug 11 2003

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All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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