Chinese Journal of Organic Chemistry >
Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives
Received date: 2014-10-31
Revised date: 2015-01-20
Online published: 2015-02-02
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).
Pyropheophorbide-a methyl ester was used as a starting material. The active reaction regions were constructed by chemical modifications on the five-membered exocyclic ring, and the interconnections through different carbon chain between 132- and 17-position were carried out by classic reaction, such as intramolecular interesterification, Michael addition and Claisen condensation, to form bicyclic or spirocyclic structures in the side of C-D ring. The aminolysis and acylation were performed making use of chemical activity of end ester group at 17-position to establish the different chemical structures in the far end of chlorin chromophore. The syntheses of 9 unreported chlorins related to chlorophyll with novel carbon skeleton were accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra.
Key words： chlorophyll-a; pyropheophorbide; chlorin; chemical reaction; synthesis
Li Jinghua , Cheng Jianjun , Zhang Peng , Wu Jin , Jin Yingxue , Wang Jinjun . Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1294 -1301 . DOI: 10.6023/cjoc201410047
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