151258-40-1Relevant articles and documents
Synthesis of anti- and syn-Diol Epoxides of trans-4,5-Dihydro-4,5-dihydroxybenzofluoranthene and trans-9,10-Dihydro-9,10-dihydroxybenzofluoranthene
He, Zhen-Min,Rice, Joseph E.,LaVoie, Edmond J.
, p. 1784 - 1789 (2007/10/02)
The preparation of diastereomeric anti- and syn-epoxides of benzofluoranthene (BjF) 4,5- and 9,10-dihydrodiols is described.The anti-diol epoxides were prepared from the corresponding dihydrodiols by epoxidation with m-chloroperbenzoic acid.The isomeri
Synthesis of the Major Metabolic Dihydrodiols of Benzofluoranthene
Rice, Joseph E.,Shih, Hsien-Cheng,Hussain, Nalband,LaVoie, Edmond J.
, p. 849 - 855 (2007/10/02)
Syntheses are described for the major dihydrodiol metabolites of benzofluoranthene. trans-4,5-Dihydro-4,5-dihydroxybenzofluoranthene was prepared via 9-methoxy-11H-benzofluorene.Two of the intermediates in this synthetic sequence, 4-hydroxybenzofluoranthene and benzofluoranthene-4,5-dione, are also suspect metabolites of the parent hydrocarbon.An improved synthesis for trans-9,10-dihydro-9,10-dihydroxybenzo-fluoranthene is described.The key steps in this preparation are the Wittig reaction of acenaphthenequinone with (3-methoxyphenethyl)triphenylphosphonium bromide and the cyclization-dehydration of the intermediate, forming 10-methoxybenzofluoranthene exclusively.The synthesis of trans-2,3-dihydro-2,3-dihydroxybenzo-fluoranthene was accomplished through the intermediacy of 1,12c-dihydrobenzofluoranthen-3(2H)-one.This ketone was converted to its α-phenylseleno derivative which underwent selenoxide elimination in basic hydrogen peroxide, forming benzofluoranthene-2,3-dione directly.In each synthesis reduction of the appropriate quinone with potassium borohydride afforded the desired dihydrodiol.
