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Title: Ortholactone spiroketal fragment coupling
Author: Baddeley, Kate
ISNI:       0000 0004 6423 2329
Awarding Body: Queen's University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2017
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A divergent synthesis of spiroketals has been developed via the coupling of ortholactone and allylsilane fragments. This work expands upon earlier efforts into an intramolecular silyl modified sakurai reaction reported by Marko et al. The route provides a simple approach towards the divergent synthesis of complex structures which could be used in the synthesis of natural products and pharmaceutical molecules. The scope of this reaction has been amplified by the development of a novel methodology towards the synthesis of ortholactones via an oxidative catalytic nucleopalladation system which has allowed for the synthesis of a vast range of synthetically useful and highly functionalised ortholactones from readily accessible dihydropyran building blocks. The utility of these highly functionalised ortholactones is also demonstrated in a stereoselective rearrangement to form a substantial number of gamma-lactone structures, which are a common motif in a wide variety of natural products.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available