Synthetic studies on natural and non-natural compounds

PART I: THE STUDY OF CYCLOBUTYL SMALL RING COMPOUNDS This part of the thesis describes a variety of routes that were attempted in the quest for a polymer containing cyclobutane rings which might have unusual properties as a conductor. These methods include the utilisation of the McMurry reaction, the Wittig reaction and the Barton-Kellog reaction. An attempt at zinc carbenoid carbonyl coupling was also performed. 3-t-Butoxycyclobutenone was successfully prepared as the potential "monomer" but all methods employed to obtain the polymeric material were unsuccessful. PART II: MAPPING THE MELATONIN RECEPTOR Melatonin, N-acetyl-5-methoxytryptamine, is the principal neurohormone secreted by the pineal gland. The indoleamine plays an important role in circadian and seasonal rhythm control in many animals. To investigate the mode of action of melatonin at cellular level, a number of indole derivatives have been synthesised to map the melatonin receptor. We continued this study by the preparation of compounds substituted at C-6 and C-7 of the indole nucleus. The compounds were tested for binding affinity on mT1 and MT2 cell lines and for potency on Xenopus melanophores. These compounds provide a further understanding of the nature and shape of the receptor pocket around these regions