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 MoreCeresking Ecology & Technology co.,ltd
Contact:86 22 66218397
Address:Room 1613, Zheshang Mansion, No. 1988, Yingbin Avenue, Binhai New District, Tianjin,China.
SHIJIAZHUANG HENRYTE CHEMICALS CO,.LTD(expird)
Contact:+86-311-85208698 311-80837698
Address:NO.166, yuhua west road, SHIJIAZHUANG, China
Liaoning Yufeng Chemical Co.,Ltd.
Contact:86-0419-3418888
Address:The metallurgical industrial zone,shoushan town, Liaoyang, Liaoning, China
Contact:86-574-26865651
Address:529 YuanBaoShan Road, Beilun District
Contact:+49-9398-993127
Address:Untertorstr. 27
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)
