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Title: Biomimetic synthesis of brevianamide alkaloids
Author: Godfrey, Robert Cracknell
ISNI:       0000 0004 7969 4534
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2019
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The brevianamides are a family of fungal derived prenylated indole alkaloids. Their range of complex structures are accompanied by a diverse array of biological activity. The brevianamides were the first reported examples of the wider bicyclo[2.2.2]diazaoctane class of natural products, which have been of continued interest due to their impressive polycyclic structures and the potential role of Diels-Alderase enzymes in their biogenesis. Despite prolonged synthetic attention, several important brevianamides have yet to succumb to total synthesis and many aspects of their biosynthesis remain unclear. This thesis describes our biomimetic synthetic studies towards these complex natural products, which has resulted in several short and efficient total syntheses. These syntheses have been enabled by a substantially improved synthesis of key intermediates, which are of general utility for the wider family of natural products.
Supervisor: Lawrence, Andrew ; Lusby, Paul Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: organic chemistry ; organic synthesis ; total synthesis ; natural products ; biomimetic synthesis ; alkaloids