Pyrroles and related compounds. Part XXXI. Porphyrin ketones
The synthesis of 4,6,8-triethyl-2-methoxycarbonyl-1,3,5,7-tetramethylporphin (2a) via the e,c-biladiene route is reported. Treatment of the corresponding acid chloride (2c) with diazomethane afforded the diazo-ketone (2d) which furnished the porphyrin ketone (2e) when treated with triheptylborane. With sodium borohydride, the alcohol (2f) was obtained, thereby opening up a definitive route to the hydroxyalkyl type of substituent which is favoured in some proposals for the structure of haem-a.
Publication Source (Journal or Book title)
Journal of the Chemical Society, Perkin Transactions 1
Jones, R., Kenner, G., & Smith, K. (1974). Pyrroles and related compounds. Part XXXI. Porphyrin ketones. Journal of the Chemical Society, Perkin Transactions 1, 531-534. https://doi.org/10.1039/p19740000531