| Summary: | <p>This thesis describes the development of synthetic routes to investigate the relative and absolute
stereochemistry of a number of piperidine alkaloids isolated from Microcos Paniculata. This thesis
then goes on to explore an intramolecular Diels-Alder reaction, and explores its applicability to
natural product synthesis.</p>
<p><b>Chapter 1</b> introduces the biological significance of piperidine alkaloids, followed by a brief review
of noteworthy chemical syntheses of piperidine and (piperidine-containing) natural products.</p>
<p><b>Chapter 2</b> describes the isolation of Microcosamine A, and previous synthetic efforts towards the
alkaloid. The chapter then describes the development and optimisation of a synthetic route to the
alkaloid, culminating with independent verification of its relative and absolute configuration.</p>
<p><b>Chapter 3</b> describes the isolation, synthesis, and independent assessment of relative and absolute
configuration of Microgrewiapines AꟷC, natural products from Microcos Paniculata.</p>
<p><b>Chapter 4</b> presents corrected 1H NMR data for the originally isolated sample of the alkaloid
microconine. The asymmetric synthesis of the two C(3) epimeric forms of this compound are
presented which allow the unambiguous assignment of relative and absolute configuration.</p>
<p><b>Chapter 5</b> describes the exploration of an intramolecular Diels Alder reaction using substrates
derived from the amine ring opening of benzene oxide. Initial experiments use N-substituted allyl
amines, which perform a ring opening and spontaneous cycloaddition in 1 step to yield racemic
tricycles. Later an enantiopure route is developed utilising ring opening with a chiral amine.</p>
<p><b>Chapter 6</b> contains full experimental procedures and characterisation data for all compounds
synthesised in Chapters 2–5. </p>
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