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All data are separated in chapters. Within all chapters, all synthesised molecules are numbered and are fully characterised (IR, NMR, LCMS, GCMS) into an individual folder. The incorporation of oxygen and nitrogen atoms into a molecular skeleton is highly important in organic synthesis as many bioactive compounds contain heteroatoms within their structure. Endoperoxides are versatile molecules that are present among natural and bioactive compounds and can be used to introduce oxygen atoms during syntheses. The aim of this thesis was to investigate the reactivity of 3,6-dihydro-1,2-dioxines to generate enantioenriched and potentially bioactive compounds. A novel domino Kornblum-DeLaMare/aza-Michael reaction of 1,2-dioxines with secondary and tertiary amines was developed and this reaction found its application in the synthesis of (±)-HPA-12, an inhibitor of the CERT protein. A library of HPA-12 bioisosteres and enantioenriched compounds were generated and biologically tested. |
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