Reduced isoquinolines have been shown to exhibit marked analgesic activity, thus establishing themselves as worthy synthetic targets. Nitrile oxide 1,3-dipolar additions to 1-phenylthio-l,3-butadier: a gave 3-substituted-5-(2-phenylthioethen-l-yl)-2-isoxazolines, whirr on reduction afforded the corresponding amino-alcohols. Further modification gave rise to 5-amino-a,5-unsaturated aldehydes. Unfortunately, the requisite Diels-Alder reaction of these aldehydes to give precursors of reduced isoquinolines did not meet with success. However, intramolecular Diels-Alder cycloaddition of ethyl 7acrylamido-2,4-octadienoate gave the desired isoquinoline skeleton. Synthetic approaches to-the Strychnos, indole alkaloid retulinal were also carried out, centering on the preparation of a model compound, (Z)-8-ethylidine-5-formyl-2,3,3a,6,7,7a-hexahydro-3a-phenyl1,6-ethano-lH-indole. A key intramolecular nitrile oxide addition failed due to nitrile oxide dimerisation. However, an approach based on a Claisen rearrangement followed by an amine to ester cyclisation produced the desired ethanoindole framework. Studies were then directed towards the synthesis of retulinal.