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Title: Synthetic investigations of oxygen heterocyclic compounds
Author: Ayoub, M. T.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1978
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Chapters 1 and 2 of this thesis contain a review of recent research in the but-3-enolide field, with particular emphasis on naturally occurring compounds. Chapter 3 describes the successful direct synthesis of methyl tetronate in high yield by cyclisation of ethyl 4-bromo-3-methoxy-but-2-enoate. Metallation of methyl tetronate at carbon atom 5, with lithium di-isopropyl amide also in high yield, was successfully accomplished, and the anion so generated was used to prepare arylidene- and cinnamylidene-butenolides and related compounds by condensation with a number of appropriate alkylating and acylating agents. Liperolide, shown to be identical to the naturally occurring compound, was also prepared by application of this method. Chapter 4 is a comprehensive survey of the 13C N.M.R. spectra of tetronic acids, butenolides, and 2-pyrones. 13C N.M.R. is shown to be a very effective tool in distinguishing five-membered ring butenolides and six-membered ring 2-pyrones - a hitherto very difficult task by 1H N.M.R.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available