Stereochemical studies on porphyrin a: assignment of the absolute configuration of a model porphyrin by degradation
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 1565-1580
- https://doi.org/10.1039/p19860001565
Abstract
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.This publication has 3 references indexed in Scilit:
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