M.Sc. (Chemistry) / The name monatin was given to the sweet compound isolated from the roots of the plant Schlerochiton ilicifolius as a mixture of salts, predominantly the sodium salt. The structure of monatin was previously determined by high- field 1 Hand 13 C n . m. r . spectra and confirmed by single crystal X- ray crystallography. The problem of the absolute stereochemistry of monatin did, however, remain unanswered. Several experiments were carried out which provides additional evidence on the relative and absolute stereochemistry of monatin. An approach to the total synthesis of monatin is described. The first phase of this work involves the development of methods for the synthesis of a key intermediate, 1- methyl 2-amino-5- (3'- indolyl)-4-oxopentanoate, using a coupling reaction. The second phase of the synthesis involves the addition of a carboxylic acid equivalent to the ketone group of the coupled product. The final synthetic product was compared with a natural monatin derivative.
| Identifer | oai:union.ndltd.org:netd.ac.za/oai:union.ndltd.org:uj/uj:4316 |
| Date | 13 March 2014 |
| Creators | Olivier, Johan |
| Source Sets | South African National ETD Portal |
| Detected Language | English |
| Type | Thesis |
| Rights | University of Johannesburg |
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