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Title: Development of a dual Fries-Claisen rearrangement strategy
Author: Garcia-Torres, Jason
ISNI:       0000 0004 2724 1891
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 2012
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Synthetic approaches towards linear fused carbon rings have been developed over the last decades due to their high interest as compounds with potential antibiotic activity and as organic electronics. The application of a novel iterative route towards linear fused carbon ring systems could provide a versatile new mode of access to complex substituted ring systems. Studies have previously demonstrated the use of an allylation-double Claisen-RCM sequence to build fused carbon rings (C). In this thesis we described our work to expand the use of this methodology by developing milder reaction conditions that could be applied to a wider range of compounds. This novel methodology was applied towards the synthesis of benzodifuran compounds (D). Our work was extended by developing, for the first time, a mixed Fries-Claisen rearrangement strategy which furnishes template (F), a key intermediate in the synthesis of pyranonaphthoquinones (G). Our work culminated in a new approach to the pyranonaphthoquinone natural products eleutherin (H) and isoeleutherin (I). [Figures missing from abstract].
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Fries rearrangement ; Claisen rearrangement ; Pyranonaphthoquinones ; Tetracyclines ; Linear fused carbon rings