Synthetic Approaches to Medium and Large Rings

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

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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

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