Chinese Journal of Organic Chemistry >
Regio- and Stereoselective Aryl(aroyl)methylenenation of Pyropheophorbide and Syntheses of Chlorophyllous Chlorin Derivatives
Received date: 2021-09-30
Revised date: 2021-12-29
Online published: 2022-01-21
Supported by
National Natural Science Foundations of China(21272048); Natural Science Foundation of Shandong Province(ZR2015BQ012)
Using the pyropheophorbide-a methyl ester as the starting material, the formyl group and α-diketone moiety were introduced into the water-soluble end of the N21-N23 axis of the macrocyclic chromophore at different positions by the allomerization on the exocyclic ring ketone. Based on the cross-aldol condensation, the regio- and stereoselective aryl(aroyl)methylenations of pyropheophorbide-a were accomplished on the exocyclic ring and at C12-position. A series of unreported chlorin derivatives that contain the aryl(aroyl)ketene unit were synthesized. In addition, the formation mechanism, stereoisomerism and the optical properties of the aryl(aroyl)methylenated products were discussed. The chemical structures of all newly synthesized compounds were characterized by elemental analysis, MS, UV-Vis and 1H NMR spectra.
Na Gao , Xiaohui Chu , Yang Liu , Jiazhu Li , Jinjun Wang . Regio- and Stereoselective Aryl(aroyl)methylenenation of Pyropheophorbide and Syntheses of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1111 -1122 . DOI: 10.6023/cjoc202109052
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