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Communication | Special issue | Vol 44, No. 1, 1997, pp.89-93
Published online, 1st January, 1970
DOI: 10.3987/COM-96-S21
Synthesis of a Fluorine Analog of Hematoporphyrin by Ring Closure

Masaaki Omote, Akira Ando, Toshiyuki Takagi, Mayumi Koyama, and Itsumaro Kumadaki*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101, Japan

Abstract

Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoroacetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxy group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboate (10). Both esters were condensed to a dipyrrolomethane compound (11), which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give a hexafluorohematoporphyrin derivative (14), potentially useful for photodynamic therapy of cancer.