Studies in Natural Product Chemistry

Warnock, William D. C (1967) Studies in Natural Product Chemistry. PhD thesis, University of Glasgow.

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This thesis is concerned with the structural elucidation of three tetranortriterpenoids and interconversion studies in this field. It is prefaced by a review of the tetranortri-terpenoids. The configuration and stereochemistry of two monoterpene alkaloids are also derived. Part I. The constitution and stereochemistry of swietenolide (A), a bitter principle from the seeds of Swietenia macrophylla, a Central American timber of the family Meliaceae, are deduced from its chemical and spectroscopic behaviour and confirmed by degradative correlation with mexicanolide. The structures of two other tetranortriterpenoids from the heartwood of Khaya grandifoliola, a West African member of the same family, are shown to be 6-hydroxy methyl angolensate (B) and 6-acetoxy methyl angolensate (C) by analysis of their single and double resonance N. M. R. spectra. Part II. Experiments designed to support present theories on the biogenesis of tetranortriterpenoids possessing the bicyclononanolide ring system, as typified by swietenolide, are described. Attempts were made to achieve in vitro conversion of two naturally occurring tetranortriterpenoids into-mexicanolide by formation of the C-2/C-30 bond, a key step in the proposed biogenesis. Part III. The constitution and stereochemistry of hydroxyskytanthines I (D) and II (E), two minor alkaloids of Skytanthus acutus, a plant native to the Chilean Atacama desert, are established on the basis of single and double resonance N. M. R. and infrared spectroscopy and mass spectrometry. The chemistry and biosynthesis of Skytanthus alkaloids is also reviewed.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1967
Depositing User: Enlighten Team
Unique ID: glathesis:1967-78449
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 30 Jan 2020 15:22
Last Modified: 30 Jan 2020 15:22

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