- Synthesis, absolute configuration, and bacterial mutagenicity of the 8 stereoisomeric vicinal diol epoxides at the terminal benzo ring of carcinogenic dibenz[ a,h ]anthracene
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The synthesis of the 8 possible stereoisomeric diol epoxides (DEs) at the terminal benzo ring of carcinogenic dibenz[a,h]anthracene (DBA) is reported. trans-3,4-Dihydroxy-3,4-dihydro-DBA (1) afforded the 4 bay region DEs: the enantiomeric pairs of the ant
- Frank, Heinz,Funk, Mario,Oesch, Franz,Platt, Karl L.
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p. 2258 - 2268
(2012/06/15)
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- Reduction of ortho-Quinones to Dihydrodiols
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1,2-Naphthaquinone, 5-bromo-1,2-naphthaquinone and dibenzanthracene-3,4-quinone in the form of dibromo-intermediates were reduced to a mixture of cis- and trans-diols by the action of sodium borohydride in ethanol.An alternative synthesis of trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene is also reported.
- Kundu, Nitya G.
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p. 1920 - 1923
(2007/10/02)
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- Synthesis of Biologically Active Metabolites of Dibenzanthracene
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Syntheses are described of the trans 1,2- and 3,4-dihydro diol metabolites (3a and 1a) of dibenzanthracene (DBA) and the corresponding diol epoxide derivatives 4 and 2, implicated as the ultimate carcinogenic metabolites of DBA.The synheses of 1a and 3a are accomplished from DBA via lithium-ammonia reduction to 1,4,7,8,11,14-hexahydrodibenzanthracene, base-catalyzed isomerization, Prevost reaction, dehydrogenation, and basic methanolysis.This approach involves considerably fewer steps and affords superior overall yields than obtainable by more conventional methods entailing multistep ring construction.Epoxidation of 1a affords stereospecifically the anti diol epoxide isomer 2, whereas similar reaction of 3a furnishes a mixture of the corresponding syn and anti diol epoxide isomers in 3:1 ratio.Biological evidence implicates 1a and 2 as proximate and ultimate carcinogenic forms, respectively, of DBA.Synthesis of 3-hydroxydibenzanthracene, also known to be a metabolite of DBA, is also described.
- Lee, Hong Mee,Harvey, Ronald G.
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p. 588 - 592
(2007/10/02)
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