Abstract
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.