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Title: Transannular Claisen rearrangements of α-sulfonyl lactones
Author: Gore, Sophie
Awarding Body: University of London
Current Institution: Imperial College London
Date of Award: 2009
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This thesis is divided into three sections. Section one is a review of transannular pericyclic reactions. It covers the four main types of pericyclic reaction and major contributions in the field to date. Recent applications of these reactions to natural product synthesis are also included. Section two discusses the results of research efforts into transannular Claisen rearrangements of α-sulfonyl lactones. The background to the project is discussed along with initial investigations into the transannular Claisen and decarboxylative Claisen rearrangements (dCr) of the 7-membered ?-tosyl lactone to form vinyl cyclopropanes. Stereoselectivity from within the pericyclic array, by substitution at the lactone C7 position is examined. Efforts towards stereoinduction from outside of the pericyclic array are also detailed, along with aryl substitution at the lactone C5 position to form highly substituted vinyl cyclopropanes. Extension of this methodology to the unprecedented transannular Claisen rearrangement and dCr reaction of 8-membered ?-tosyl lactones to give vinyl cyclobutanes is reported. Finally, efforts towards a novel synthetic route to (?)-grandisol utilising the transannular Claisen rearrangement chemistry is described. Section three details the experimental procedures and spectroscopic data for the compounds described in section two.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available