Synthesis of Methyl Pyropheophorbide-a with Cycloheptyl(acyl)Group at 3-Position

Abstract

Methyl pyropheophorbide-a (MPP-a) was used as starting material. The carbonyl group on E-ring of methyl pyropheophorbide-d was protected and the Grignard reaction with cycloheptyl magnesium bromide was performed. The sec-alcohol obtained from Grignard reaction was subjected to deprotection, dehydration, oxidation and other more reaction for converting hydroxyl group at 3-position into carbon-carbon double bond and carbonyl group. The Grignard reaction of the carbon-oxygen double bond and following dehydration were carried out to form olefin. The synthesis of a series of new methyl pyropheophorbide-a substituted by cycloheptyl group at 3-position was completed. The structures of the compounds were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

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

Cite this article

WANG Jin-Jun*^,1,LIU Wan-Hui²,HAN Guang-Fan³,SHIM Yong Key⁴. Synthesis of Methyl Pyropheophorbide-a with Cycloheptyl(acyl)Group at 3-Position[J]. Chin. J. Org. Chem., 2005, 25(01): 65-70.

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3-位环庚烷(酰)基取代的焦脱镁叶绿酸-a甲酯的合成