Traegeric Acid and Other Metabolites of Aspergillus flaschentraegeri

Bell, Alan Menzies (1971) Traegeric Acid and Other Metabolites of Aspergillus flaschentraegeri. PhD thesis, University of Glasgow.

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Abstract

The remarkable transformation of the antifungal antibiotic traegeric acid, by means of copper sulphate in ethereal sulphuric acid, has been elucidated by inter-relation with the new norditerpene pigment flascherone, which is also produced by Aspergillus flaschentraegeri. This has allowed the structure of the antibiotic to be elaborated as an unusual diterpene pseudo-acid. Esterification of the antibiotic led to a variety of products depending on the conditions. Formation of one product obtained with diazomethane was shown to involve attack at the enone system to give a cyclopropyl ketone grouping. Varied chemical transformations of this compound, including reductive studies and ozonolysis have established the relative configuration at 2 of the asymmetric centres, and afforded evidence concerning the remaining centres. Routes to heavy atom and mono-carbonyl derivatives for X-ray and ORD work, respectively, have been investigated. The known anthraquinone physcion and a related pigment have been isolated from the fungus. The demonstration of nuclear overhauser effects in the n. m. r. spectrum of the latter has played a part in establishing its structure as the first C-prenylated anthraquinone. A phthalic acid metabolite has been characterised and synthetic studies on it carried out.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry, Biochemistry
Date of Award: 1971
Depositing User: Enlighten Team
Unique ID: glathesis:1971-78566
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 28 Feb 2020 12:09
Last Modified: 28 Feb 2020 12:09
URI: http://theses.gla.ac.uk/id/eprint/78566

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