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Title: Exploration of 8-membered lactones in synthesis
Author: Harrison, J. R.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1997
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This dissertation details the synthesis of a range of 8-membered lacones via a Claisen rearrangement route and also efforts towards the synthesis of 8-membered lactones by a new radical cyclisation strategy. Chapter One reviews the effect of substituents on the rates and stereoselectivities of Claisen rearrangements. Chapter Two describes the synthesis of 8-membered lactones, such as 2.43d, 2.109 and 2.85 by Claisen rearrangement methodology. Potential application of this methodology to the synthesis of the immunosuppressant discodermolide is also discussed. (Fig. 3864A) Chapter Three reviews the use of radical cyclisation in the formation of medium- and large-ring lactones. Studies on a new method of 8-membered lactone preparation by the radical cyclisation of the allylstannane 4.47 are reported in Chapter Four (Fig. 3864B).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available