Abstract

23
A. R. Battersby, K. S. Cardwell and F. J. Leeper
"Stereochemical Studies on Porphyrin a: Assignment of the Absolute Configuration of a Model Porphyrin by Degradation"
J. Chem. Soc., Perkin Trans. 1,1986, 1565-1580. Full Text

The synthesis is described of a porphyrin alcohol (22) which has a structure very similar to that of porphyrin a (2). The model porphyrin was resolved by separation of its camphanate esters. Ozonolysis of the 2-nitrobenzoate of each enantiomer in tritiated form gave a derivative of 2- hydroxypentanedioic acid whose configuration was determined by dilution analysis. It is demonstrated that correlation of the stereochemistry of porphyrin a with that of the model (22) will be possible by means of the ¹H and ¹⁹F n.m.r. spectra of the corresponding esters with (-)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid.

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