The aim of the project is to synthesise (-)-morphine utilising aziridine and metathesischemistry. The thesis is divided into three chapters.Chapter 1 provides brief reviews on the subjects of total synthesis of morphine; ringrearrangementmetathesis (RRM) and regioselective ring-opening of aziridines.Chapter 2 focuses on the research findings in the past three years. Two routes, A and B,were investigated in attempts to synthesise morphine (Scheme 1). In route A, sulfonylcyclopentene II was prepared from ring-closing metathesis of a diene precursor, whichwas synthesised from lithiated cinnamylsulfone and butadiene monoxide. Subsequently,RRM reactions of several [alpha]-SO2Ph allyl derivatives of II were investigated and someinteresting results were obtained. The synthesis of 2,3-trans vinylaziridine III wasachieved in seven steps beginning with a Grignard reaction of (4-methoxyphenyl)magnesium bromide with butadiene monoxide. Subsequently, somehighly regioselective ring-opening reactions of III with sulfur-stabilised anionicnucleophiles were achieved. However, in an attempt to synthesise compound I from IIand III, no reaction was observed. This led to the investigation of route B, in which fivemethods for the synthesis of compound IV were investigated. The practical approachdeployed a novel Al-mediated substitution of the 4-tosyl group of the tosyltetrahydropyridine counterpart of IV, prepared from V and III, with a phenylthio group.Chapter 3 provides the experimental details and characterisation data.Imperial Users onl
