Synthesis of optically active fjord-region 11, 12-diol 13, 14-epoxides and the K-region 9, 10-oxide of the carcinogen benzo [g] chrysene

DR Bushman, SJ Grossman, DM Jerina…

Index: Bushman, Daniel R.; Grossman, Scott J.; Jerina, Donald M.; Lehr, Roland E. Journal of Organic Chemistry, 1989 ,  vol. 54,  # 15  p. 3533 - 3544

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Citation Number: 36

Abstract

Optically pure enantiomers of the diastereomeric pair of benzo [g] chrysene-ll, l2-diol13, 14- epoxides (Scheme VI) were synthesized from (llR, 12R)-and (11S, 12S)-dihydroxy-ll, l2- dihydrobenzo [g] chrysenes (16 (R, R) and 16 (S, S)). Two routes were employed to synthesize the racemic dihydrodiol 16. Although the Prevost method for introduction of the trans-vicinal oxygen atoms at Cll and C12 of 13, 14-dihydrobenzo [g] chrysene (7) ...