2012Chinese Journal of Organic ChemistryOpen access

Allomerization of Methyl Pheophorbide-a and Synthesis of Chlorin Derivatives

Lumin Wang, Peng Wang, Chao Liu, Yingxue Jin, Jinjun Wang

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Abstract

The allomerization of methyl pyropheophorbide-a, used as starting material, was carried out under the alkaline condition to separate a series of oxidized and rearranged products at exocyclic E-ring and C-12-methyl group.The same reaction of chlorinated methyl pyropheophorbide-a also came through similar processes.The further oxidations of C-13 2 -and C-12-oxidized products gave two different results, the former reacted quickly and produced complicated compounds, the latter H H basicallyH H unchanged under the same condition.The structures of all new chlorin derivatives were characterized by elemental analysis, UV, IR and 1 H NMR spectra.The possible mechanisms about corresponding reactions were tentatively proposed.Keywords chlorophyll-a;

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The allomerization of methyl pyropheophorbide-a, used as starting material, was carried out under the alkaline condition to separate a series of oxidized and rearranged products at exocyclic E-ring and C-12-methyl group.The same reaction of chlorinated methyl pyropheophorbide-a also came through similar processes.The further oxidations of C-13 2 -and C-12-oxidized products gave two different results, the former reacted quickly and produced complicated compounds, the latter H H basicallyH H unchanged under the same condition.The structures of all new chlorin derivatives were characterized by elemental analysis, UV, IR and 1 H NMR spectra.The possible mechanisms about corresponding reactions were tentatively proposed.Keywords chlorophyll-a;

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Available abstract

The allomerization of methyl pyropheophorbide-a, used as starting material, was carried out under the alkaline condition to separate a series of oxidized and rearranged products at exocyclic E-ring and C-12-methyl group.The same reaction of chlorinated methyl pyropheophorbide-a also came through similar processes.The further oxidations of C-13 2 -and C-12-oxidized products gave two different results, the former reacted quickly and produced complicated compounds, the latter H H basicallyH H unchanged under the same condition.The structures of all new chlorin derivatives were characterized by elemental analysis, UV, IR and 1 H NMR spectra.The possible mechanisms about corresponding reactions were tentatively proposed.Keywords chlorophyll-a;

Key concepts: Chemistry, Pheophorbide A, Chlorin, Combinatorial chemistry, Organic chemistry, Photodynamic therapy

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