Synthesis of the major metabolic dihydro diols of benzo [j] fluoranthene

…, HC Shih, N Hussain, EJ LaVoie

Index: Rice, Joseph E.; Shih, Hsien-Cheng; Hussain, Nalband; LaVoie, Edmond J. Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 849 - 855

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Citation Number: 22

Abstract

Llfluoranthene was accomplished through the intermediacy of 1, 12c-dihydrobenzo~] fluoranthen-3 (2H)-one. This ketone was converted to its a-phenylseleno derivative which underwent selenoxide elimination in basic hydrogen peroxide, forming benzo~] fluoranthene-2, 3-dione directly. In each synthesis reduction of the appropriate quinone with potassium borohydride afforded the desired dihydrodiol.