Stillwell W G, Horning M G, Griffin G W, Tsang W S
Drug Metab Dispos. 1982 Jan-Feb;10(1):11-4.
The structures of three isomeric 1,2,3,4-tetrahydroxytetrahydronaphthalene metabolites of naphthalene have been confirmed by synthesis. Six isometric 1,2,3,4-tetrahydroxy-1,2,3,4-tetrahydronaphthalene structures occurring in for dl-pairs and two mesoforms have been synthesized. Five were synthesized by the action of osmium tetroxide on the cis- and trans-1,2-dihydrodiols and cis- and trans-1,4-dihydrodiols. The sixth isomeric tetrahydrotetrol was synthesized by hydrolysis of trans-1,2-dihydroxy-syn-3,4-epoxy-1,2,3,4-tetrahydronaphthalene (the syn-dihydrodiolepoxide of naphthalene). By comparing the gas-chromatographic and mass-spectrometric properties of the synthetic and urinary tetrahydrotetrols, two of the urinary metabolites were identified as 1 beta, 2 alpha, 3 alpha, 4 beta- and structure of the third tetrahydrotetrol metabolite, 1 beta, 2 alpha, 3 beta, 4 alpha-tetrahydroxy-1,2,3,4-tetrahydronaphthalene, identified in earlier studies, was confirmed.
萘的三种异构1,2,3,4 - 四羟基四氢萘代谢物的结构已通过合成得以确认。已合成出六种异构的1,2,3,4 - 四羟基 - 1,2,3,4 - 四氢萘结构，它们以dl - 对和两种内消旋形式存在。其中五种是通过四氧化锇作用于顺式和反式 - 1,2 - 二氢二醇以及顺式和反式 - 1,4 - 二氢二醇合成的。第六种异构四氢四醇是通过反式 - 1,2 - 二羟基 - 顺式 - 3,4 - 环氧 - 1,2,3,4 - 四氢萘（萘的顺式二氢二环氧物）水解合成的。通过比较合成的和尿液中的四氢四醇的气相色谱和质谱性质，确定了两种尿液代谢物为1β, 2α, 3α, 4β - 以及第三种四氢四醇代谢物1β, 2α, 3β, 4α - 四羟基 - 1,2,3,4 - 四氢萘的结构，该结构在早期研究中已被鉴定，现得以确认。
