{"id":{"repo_id":"cape-town","oai_identifier":"oai:open.uct.ac.za:11427/16406"},"canonical_url":"https://search.dev.ndltd.org/etd/cape-town/oai:open.uct.ac.za:11427/16406","repository":{"repo_id":"cape-town","name":"University of Cape Town","base_url":"https://open.uct.ac.za/oai/request"},"display":{"title":"Synthesis of delta-1(9)-octalinols and their analogues","abstract":"This project was initiated by the observation that a natural glyeoside of a triterpene, which incorporated the allylic alcoholic moiety 1 gave the novel ketone diene 2 when it was subjected to acetolysis. A number of octahydronaphthalinols (1, R=H) Δ 1 ( 9) octalinols), ' were prepared by reduction of the α, β unsaturated octalones obtained from cyclohexanones condensed with α, β -unsaturated ketones. These octalinols were characterised as their acetates (1, R=Ac). The attempts to convert these to the desired ketone dienes 2 by reaction with mixtures of acetic anhydride-acetic acid-boron trifluoride proved unsuccessful. Two model compounds derived from hecogenin and incorporating the octalinol residue 1 were also prepared in the hope that the analogous ketone 2 might be obtained. This reaction, too, was unsuccessful.","abstract_html":"This project was initiated by the observation that a natural glyeoside of a triterpene, which incorporated the allylic alcoholic moiety 1 gave the novel ketone diene 2 when it was subjected to acetolysis. A number of octahydronaphthalinols (1, R=H) Δ 1 ( 9) octalinols), ' were prepared by reduction of the α, β unsaturated octalones obtained from cyclohexanones condensed with α, β -unsaturated ketones. These octalinols were characterised as their acetates (1, R=Ac). The attempts to convert these to the desired ketone dienes 2 by reaction with mixtures of acetic anhydride-acetic acid-boron trifluoride proved unsuccessful. Two model compounds derived from hecogenin and incorporating the octalinol residue 1 were also prepared in the hope that the analogous ketone 2 might be obtained. This reaction, too, was unsuccessful.","abstract_has_math":false,"creators":["Lupuwana, Lincoln L"],"institution":"Department of Chemistry","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Elsworth, J F"],"committee_chairs":[],"committee_members":[],"year":1986,"date_issued":"1986","date_published":"1986","updated_at":"2026-07-22T22:23:07Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/11427/16406","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Elsworth, J F"]},{"key":"dc:creator","label":"Author","values":["Lupuwana, Lincoln L"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2016-01-15T14:18:48Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2016-01-15T14:18:48Z"]},{"key":"dc:date.issued","label":"Date","values":["1986"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Department of Chemistry"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Cape Town"]},{"key":"dc:type","label":"Dc Type","values":["Master Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Masters"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["MSc"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/11427/16406"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Includes bibliographical references."]},{"key":"dc:description.abstract","label":"Abstract","values":["This project was initiated by the observation that a natural glyeoside of a triterpene, which incorporated the allylic alcoholic moiety 1 gave the novel ketone diene 2 when it was subjected to acetolysis. A number of octahydronaphthalinols (1, R=H) Δ 1 ( 9) octalinols), ' were prepared by reduction of the α, β unsaturated octalones obtained from cyclohexanones condensed with α, β -unsaturated ketones. These octalinols were characterised as their acetates (1, R=Ac). The attempts to convert these to the desired ketone dienes 2 by reaction with mixtures of acetic anhydride-acetic acid-boron trifluoride proved unsuccessful. Two model compounds derived from hecogenin and incorporating the octalinol residue 1 were also prepared in the hope that the analogous ketone 2 might be obtained. This reaction, too, was unsuccessful."]},{"key":"dc:title","label":"Title","values":["Synthesis of delta-1(9)-octalinols and their analogues"]}]}],"canonical_facts":{"dc:contributor.advisor":["Elsworth, J F"],"dc:creator":["Lupuwana, Lincoln L"],"dc:date.accessioned":["2016-01-15T14:18:48Z"],"dc:date.available":["2016-01-15T14:18:48Z"],"dc:date.issued":["1986"],"dc:description":["Includes bibliographical references."],"dc:description.abstract":["This project was initiated by the observation that a natural glyeoside of a triterpene, which incorporated the allylic alcoholic moiety 1 gave the novel ketone diene 2 when it was subjected to acetolysis. A number of octahydronaphthalinols (1, R=H) Δ 1 ( 9) octalinols), ' were prepared by reduction of the α, β unsaturated octalones obtained from cyclohexanones condensed with α, β -unsaturated ketones. These octalinols were characterised as their acetates (1, R=Ac). The attempts to convert these to the desired ketone dienes 2 by reaction with mixtures of acetic anhydride-acetic acid-boron trifluoride proved unsuccessful. Two model compounds derived from hecogenin and incorporating the octalinol residue 1 were also prepared in the hope that the analogous ketone 2 might be obtained. This reaction, too, was unsuccessful."],"dc:identifier.uri":["http://hdl.handle.net/11427/16406"],"dc:language.iso":["eng"],"dc:publisher.department":["Department of Chemistry"],"dc:publisher.institution":["University of Cape Town"],"dc:title":["Synthesis of delta-1(9)-octalinols and their analogues"],"dc:type":["Master Thesis"],"dc:type.qualificationlevel":["Masters"],"dc:type.qualificationname":["MSc"]},"updated_at":"2026-07-22T22:23:07Z"}