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Title: Synthetic applications of nitrile oxide-olefin dipolar additions
Author: Lathbury, David Charles
ISNI:       0000 0001 3605 413X
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 1983
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry