TY - JOUR
T1 - Synthesis of dihydrodiol metabolites of naphtho[8,1,2-ghi]chrysene and dibenzo[c,mno]chrysene
AU - Sharma, Arun
AU - Krzeminski, Jacek
AU - Desai, Dhimant
AU - Amin, Shantu
N1 - Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2003
Y1 - 2003
N2 - 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.
AB - 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.
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U2 - 10.1080/10406630308050
DO - 10.1080/10406630308050
M3 - Article
AN - SCOPUS:0042766396
SN - 1040-6638
VL - 23
SP - 297
EP - 305
JO - Polycyclic Aromatic Compounds
JF - Polycyclic Aromatic Compounds
IS - 3
ER -