Synthetic Approaches to Medium and Large Rings

Kennedy, William Brian (1974) Synthetic Approaches to Medium and Large Rings. PhD thesis, University of Glasgow.

Abstract

Synthetic routes to macrocyclic ketones and lactones via fused bicyclic, doubly bridged tricyclic and bridged tricyclic precursors have been investigated as follows : (a) The condensation of diethylsuccinylsuccinate and acrolein gave two interesting compounds. The first compound was identified as a fused tricyclic system, an oetahydroindacene-dione-dicarboxylic ester, whose structure was investigated and the ester groups found to be trans. The second was a complex bridged tetracyclic system, whose structure was elucidated by chemical and physical methods, including 13-C nmr spectroscopy, (b) The synthesis of cycloalkynones was investigated from Delta2,6-tricyclo-[6,3,1,0 2,6]-dodecan-5,12-diones by cleavage of the one-carbon bridge, followed by cleavage of the double bond by Eschenmoser's tosylhydrazone-epoxide ring opening reaction. The first half of this sequence was shown to be feasible, but lack of time precluded further investigation. A direct approach to macrocyclic lactones from Delta9-tetrahydrochroman-4-ones was not successful.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1974
• Depositing User: Enlighten Team
• Unique ID: glathesis:1974-78669
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:04
• Last Modified: 30 Jan 2020 15:04
• URI: https://theses.gla.ac.uk/id/eprint/78669