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Some Studies in the Chemistry of Substituted Azetinone and Pyrroloindole-Carboxylic Acids

Chan, Chat On; (1991) Some Studies in the Chemistry of Substituted Azetinone and Pyrroloindole-Carboxylic Acids. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

This thesis is concerned with the chemistry of azetidinone carboxylic acids and pyrrolodine carboxylic acids and their derivatives. As such, the introduction surveys the general field of β-lactam biochemistry, the more specific area of carbapenem synthesis and the chemistry of pyrroloindole-2-carboxylic acids. The first main section of the thesis describes the free-radical chemistry of azetidin-2-one-4-carboxylic acids and the attempted elaboration of these materials into precursors to the carbapenem antibiotic methylthienamycin. The second section involves an investigation into both the one and two electron chemistry of pyrroloindole-2-carboxylic acids. Various derivatives of these acids were also synthesized in an attempt to elucidate the mechanism for the high stereoselective formation of the endo-isomer. The oxidative cleavage of the indole ring of tryptophan derivatives was investigated resulting in enantiospecific syntheses of R- and S-methyl aspartic acids. During the course of these studies, a crystalline mixed anhydride was isolated from reaction of a carboxylic acid with a chloroformate and its structure determined by single crystal X-ray analysis.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Some Studies in the Chemistry of Substituted Azetinone and Pyrroloindole-Carboxylic Acids
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
URI: https://discovery.ucl.ac.uk/id/eprint/10122690
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