111139-21-0Relevant articles and documents
Stereochemical Studies on Porphyrin a: Assignment of the Absolute Configuration of a Model Porphyrin by Degradation
Battersby, Alan R.,Cardwell, Kevin S.,Leeper, Finian J.
, p. 1565 - 1580 (2007/10/02)
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-hydroxypentadioic 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 (1)H and (19)F n.m.r. spectra of the corresponding esters with (-)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid.