Grignard Reaction on E-Ring of Methyl Pyropheophorbide-a and the Synthesis of Its Deoxy-derivatives

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (6): 663-668. Previous Articles Next Articles

焦脱镁叶绿酸-a甲酯的E-环格氏反应及其脱氧衍生物的合成

纪建业^a, 王进军^*,b, 王鲁敏^b, 韩光范^c, 沈荣基^d

^a通化师范学院化学系通化 134002
^b烟台大学应用化学系烟台 264005
^c华东船舶工业学院材料科学与工程学院镇江 212003
^d仁济大学釜山韩国

收稿日期:2003-08-25 修回日期:2003-12-14 接受日期:2003-12-16 发布日期:2022-09-21
通讯作者: ^*E-mail: wjj1955@163.com
基金资助:
科技部中韩政府间合作项目(2002)资助项目.

Grignard Reaction on E-Ring of Methyl Pyropheophorbide-a and the Synthesis of Its Deoxy-derivatives

JI, Jian-Ye^a, WANG, Jin-Jun^*,b, WANG, Lu-Min^b, HAN, Guang-Fan^c, SHIM, Young Key^d

^a Department of Chemistry, Tonghua Teachers College, Tonghua 134002
^b Department of Applied Chemistry, Yantai University, Yantai 264005
^c School of Material and Environmental Engineering, East China Shipbuilding Institute, Zhenjiang 212003
^d Lnje University, Pusan, Korea

Received:2003-08-25 Revised:2003-12-14 Accepted:2003-12-16 Published:2022-09-21

Abstract

Methyl pyropheophorbide-a and its derivatives substituted by formylmethyl at 3-position were used as starting material for thesynthesis of title compounds. The carbonyl groups at 13¹-position were converted into alkyhydroxy groups by means of Grignard reaction with straight or cyclic alkyl magnesium bromide. The exocyclic carbon-carbon double bond was formedby dehydration reaction to give mono(di)alkylmethylenesubstituted 13¹-deoxypyropheophorbide derivatives. The stereochemistry of the Grignard reaction onthe E-ring was discussed. The structures of all these new compounds were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: methyl pyropheophorbide-a, Grignard reaction, dehydration, photodynamic therapy (PDT)

Cite this article

JI, Jian-Ye, WANG, Jin-Jun, WANG, Lu-Min, HAN, Guang-Fan, SHIM, Young Key. Grignard Reaction on E-Ring of Methyl Pyropheophorbide-a and the Synthesis of Its Deoxy-derivatives[J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 663-668.

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焦脱镁叶绿酸-a甲酯的E-环格氏反应及其脱氧衍生物的合成

Grignard Reaction on E-Ring of Methyl Pyropheophorbide-a and the Synthesis of Its Deoxy-derivatives

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