Regioselective transformation of octaethylporphyrin into a phytoporphyrin analogue.

Abstract

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.

• Authors: Michio Kunieda, Yuji Mikata, Hitoshi Tamiaki
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 72 Issue 19 Pg. 7398-401 (Sep 14 2007) ISSN: 0022-3263 [Print] United States
• PMID: 17705539 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Porphyrins
• Pyrroles
• octaethylporphyrin
• Chlorophyll
• phytoporphyrin
• chlorin

Topics

• Chlorophyll (analogs & derivatives, chemical synthesis, chemistry)
• Porphyrins (chemical synthesis, chemistry)
• Pyrroles (chemical synthesis, chemistry)