Pyrroles and related compounds. Part XXX. Cyclisation of porphyrin β-keto-esters to phaeoporphyrins
Abstract
Porphyrin β-keto-esters are cyclised to the corresponding phaeoporphyrins in high yield by treatment of the former with 2 equiv. of thallium(III) trifluoroacetate, followed by photolysis and demetallation. In this way, the first formal total syntheses of phaeoporphyrin-a5 dimethyl ester (6a) and 2-vinylphaeoporphyrin-a5 dimethyl ester (6b) have been accomplished.