Journal of the Chemical Society. Perkin transactions I p. 1477 - 1482 (1981)
Update date:2022-08-03
Topics:
Boyd, Derek R.
Greene, Ruth M. E.
Neill, John D.
Stubbs, Michael E.
Yagi, Haruhiko
Jerina, Donald M.
trans-3,4-Dihydroxy-1,2,3,4-tetrahydrophenanthrene (11) and cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene (12) have been prepared in optically pure form via: (i) chromatographic separation of the trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrophenanthrene diastereoisomers (7a), (7b), (ii) conversion of (7a) into the optically pure (+)-tetrahydro-3,4-epoxide (8), (iii) acid-catalysed hydrolysis of (+)-(8) by attack at C-4 to yield (+)-trans-(11) and (-)-cis-(12).Several lines of evidence, including spectral methods and chemical transformation to compounds of known absolute stereochemistry, have been used to assing absolute stereochemistry to all chiral compounds described in the present study.The availability of optically pure diols (11) and (12) has allowed the absolute stereochemistry of the trans- and cis-3,4-dihydrodiol metabolites of phenanthrene (4) and (2) to be determined as (-)-(3R,4R) and (+)-(3S,4R) respectively.Phenanthrene 3,4-oxide,an initial mammalian metabolite of phenanthrene prepared from optically pure precursors, was optically active but racemized spontaneously at ambient temperature.
View MoreShanghai agrotree chemical co.,ltd.
Contact:+86-21-50117563
Address:Room 8A,liangfeng building,No.8 dongfang RD.pudong,shanghai,China
Contact:+86-532-55689660
Address:qingdao
Mollt Biochem Co., Ltd(expird)
Contact:+86-21-38682181
Address:shanghai ,china
Jiangsu Fengshan Group Co., Ltd.
Contact:86-25-86558671
Address:1903,Central International Mansion 105-6 North Zhongshan Road, Nanjing, China
Huangshi Shennong Chemical Technology Co., Ltd
Contact:+86-714-3072290
Address:Eastern industrial park , Tieshan district , Huangshi city ,Hubei province , China
Doi:10.1039/f19817701405
(1981)Doi:10.1016/S0040-4039(01)90440-X
(1981)Doi:10.1002/anie.201603399
(2016)Doi:10.1016/S0040-4039(01)90464-2
(1981)Doi:10.1016/j.jorganchem.2005.02.026
(2005)Doi:10.1021/om0342560
(2004)
