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Title: Enantioselective synthesis of 3-polyenoyltetramic acids
Author: Royles, Brodyck J. L.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1990
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The total synthesis of the 3-polyenoyltetramic acid antibiotic altamycin A has been attempted via a novel method of preparing enantiomerically pure tetramic acids. Thus two target fragments were identified: (a) the tetramic acid and (b) the polyenal fragment. The chirality present in the latter was introduced (enantioselectively) through the catalytic Sharpless epoxidation of an isomerically pure allylic alcohol. This epoxide was then elaborated, using Wittig technology, into the aforementioned polyenal unit. The chiral acid was readily available through reaction of an ester enolate with an oxazolidine-2,5-dione of desired stereochemistry. The coupling of these fragments was studied - several methods being tried then evaluated according to their expediency. This approach to altamycin A is sufficiently flexible to allow the preparation of other members of this interesting class of naturally occurring compounds.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available