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以二环[3.1.0]己烷为骨架设计了合理的合成路线,成功合成了具有NorrishⅡ型光化学特点的光化学反应前体(1R,5S)-3-羟基-6-二环[3.1.0]己基苯基甲酮(10),并通过~1H NMR,~(13)C NMR,DEPT135,H-H COSY,HMQC,HMBC,ROESY,6-H-1D-NOE,9-H-ID-NOE和HRMS等方法表征了该化合物的结构,确定了其绝对构型.应用NorrishⅡ型光化学反应,以10为底物探索了重要前列腺素中间体化合物11的合成.通过综合谱图表征和HPLC等手段测试,结果表明化合物10经过NorrishⅡ型光化学反应得到了两个具有环戊烯结构的光化学产物化合物11和12,并据此提出了反应机理.
A rational synthetic route was designed based on the bicyclo [3.1.0] hexane. The photochemical reaction precursor (1R, 5S) -3-hydroxy-6-bicyclo [3.1.0 ] Hexyl phenyl ketone (10) and analyzed by ~ 1H NMR, ~ (13) C NMR, DEPT135, HH COZY, HMQC, HMBC, ROESY, 6-H-ID-NOE, HRMS and other methods to characterize the structure of the compound and determine its absolute configuration.The synthesis of important prostaglandin intermediate compound 11 was explored by Norrish Ⅱ photochemical reaction using 10 as the substrate.It was tested by means of comprehensive spectral analysis and HPLC The results showed that two photochemical compounds 11 and 12 having cyclopentene structure were obtained through Norrish Ⅱ photochemical reaction of compound 10, and the reaction mechanism was proposed accordingly.