Thesis-2012-GarciaTorres.pdf (5.62 MB)
Development of a dual Fries-Claisen rearrangement strategy
thesis
posted on 2012-11-26, 09:26 authored by Jason Garcia-TorresSynthetic 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].
History
School
- Science
Department
- Chemistry
Publisher
© Jasón García TorresPublication date
2012Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.EThOS Persistent ID
uk.bl.ethos.561193Language
- en