Regioselective transformation of octaethylporphyrin into a phytoporphyrin analogue.
An octaethylporphyrin derivative, 1, possessing an exo-five-membered ring fused at the 13- and 15-positions was oxidized by osmium tetroxide to give two isomeric chlorins, 3 and 5, possessing beta,beta'-dihydroxy groups at the A- and C-rings, respectively. Single dehydration of 2,3-dihydroxychlorin 3 gave a mixture of 2- and 3-(1-hydroxyethyl)porphyrins 7, while that of 12,13-dihydroxychlorin 5 resulted in the sole formation of 131-hydroxyporphyrin 9. The latter was modified smoothly to the phytoporphyrin analogue 2, whose molecular skeleton was similar to that of naturally occurring chlorophylls possessing a 131-oxo group fixed on an exo-five-membered ring.
Kunieda
Michio
M
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Mikata
Yuji
Y
Tamiaki
Hitoshi
H
D002734:Chlorophyll / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry
D011166:Porphyrins; D011758:Pyrroles; C488938:octaethylporphyrin; D002734:Chlorophyll; C008904:phytoporphyrin; C006969:chlorin