{"id":{"repo_id":"sheffield-hallam","oai_identifier":"oai:shura.shu.ac.uk:19630"},"canonical_url":"https://search.dev.ndltd.org/etd/sheffield-hallam/oai:shura.shu.ac.uk:19630","repository":{"repo_id":"sheffield-hallam","name":"Sheffield Hallam University","base_url":"https://shura.shu.ac.uk/cgi/oai2"},"display":{"title":"Synthesis of thromboxane A2 analogues.","abstract":"The aim of the project was to synthesize novel thromboxane A2 analogues which would be potential thromboxane A2 antagonists. Three thromboxane A2 analogues were synthesized, methyl 7-[-5-(3-hydroxy-1-(E)-octenyl)-2-methylbicyclo[3.3.1]non-2-en-9-yl]-[syn]-(+/-)-5-(Z)-heptenoate, methyl 7-[-5-(hydroxy-1-(E)-octenyl)-2,2-dimethylbicyclo[3.3.1]non-9-yl]-[syn]-(-+)-5-(Z)-heptenoate and methyl 7-[-5-(3-hydroxy-l-(E)-octenyl)-2,2-dimethylbicyclo[3.2.1]oct-8-yl]-[syn]-(-)-(Z)-heptenoate from a common functionalised bicycloalkane. During the synthesis of these functionalised bicycloalkanes several unexpected products were observed. These included the formation of methyl 5-methyl-6-oxa-7-oxobicyclo[3.2.2]-nonanecarboxylate during the sulphuric acid catalysed cyclisation of methyl 2-oxo-l-(3'-oxobutyl)cyclopentane-carboxylate which was contrary to the work of W G Dauben and J W McFarland and the formation of ethyl 4-methyl-bicyclo[4.4.0]dec-4,6-dienecarboxylate from the treatment of ethyl 1-(3'-methylbut-2'-ene)-2oxocyclohexanecarboxylate with stannic chloride. Another interesting rearrangement reaction was the formation of methyl 2-methine-5-oxohexanoate as well as methyl 4-oxo-3-(3'-oxobutyl)-3-tetrahydrothio-phenecarboxylate during the Michael reaction of methyl vinyl ketone with methyl 4-oxo-3-tetrahydrothiophene-carboxylate. Methyl 2-(2-methylbut-3'-en-2-yl)-3-oxo-tetrahydrothiophenecarboxylate was also an unexpected product from the alkylation of methyl 3-oxo-tetrahydrothio-phenecarboxylate with l-bromo-3-methylbut-2-ene.","abstract_html":"The aim of the project was to synthesize novel thromboxane A2 analogues which would be potential thromboxane A2 antagonists. Three thromboxane A2 analogues were synthesized, methyl 7-[-5-(3-hydroxy-1-(E)-octenyl)-2-methylbicyclo[3.3.1]non-2-en-9-yl]-[syn]-(+/-)-5-(Z)-heptenoate, methyl 7-[-5-(hydroxy-1-(E)-octenyl)-2,2-dimethylbicyclo[3.3.1]non-9-yl]-[syn]-(-+)-5-(Z)-heptenoate and methyl 7-[-5-(3-hydroxy-l-(E)-octenyl)-2,2-dimethylbicyclo[3.2.1]oct-8-yl]-[syn]-(-)-(Z)-heptenoate from a common functionalised bicycloalkane. During the synthesis of these functionalised bicycloalkanes several unexpected products were observed. These included the formation of methyl 5-methyl-6-oxa-7-oxobicyclo[3.2.2]-nonanecarboxylate during the sulphuric acid catalysed cyclisation of methyl 2-oxo-l-(3'-oxobutyl)cyclopentane-carboxylate which was contrary to the work of W G Dauben and J W McFarland and the formation of ethyl 4-methyl-bicyclo[4.4.0]dec-4,6-dienecarboxylate from the treatment of ethyl 1-(3'-methylbut-2'-ene)-2oxocyclohexanecarboxylate with stannic chloride. Another interesting rearrangement reaction was the formation of methyl 2-methine-5-oxohexanoate as well as methyl 4-oxo-3-(3'-oxobutyl)-3-tetrahydrothio-phenecarboxylate during the Michael reaction of methyl vinyl ketone with methyl 4-oxo-3-tetrahydrothiophene-carboxylate. Methyl 2-(2-methylbut-3'-en-2-yl)-3-oxo-tetrahydrothiophenecarboxylate was also an unexpected product from the alkylation of methyl 3-oxo-tetrahydrothio-phenecarboxylate with l-bromo-3-methylbut-2-ene.","abstract_has_math":false,"creators":["Evans, Elizabeth Hannah."],"institution":"Sheffield Hallam University (United Kingdom).","degree_name":"phd","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1984,"date_issued":"1984","date_published":"1984","updated_at":"2026-07-24T06:31:21Z","subjects":[],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Evans, Elizabeth Hannah."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1984"]},{"key":"dc:date.issued","label":"Date","values":["1984"]},{"key":"dc:publisher.commercial","label":"Dc Publisher Commercial","values":["Sheffield Hallam University,"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Department of Chemistry."]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["Sheffield Hallam University (United Kingdom)."]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://shura.shu.ac.uk/19630/"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["phd"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://shura.shu.ac.uk/19630/1/10694511.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The aim of the project was to synthesize novel thromboxane A2 analogues which would be potential thromboxane A2 antagonists. Three thromboxane A2 analogues were synthesized, methyl 7-[-5-(3-hydroxy-1-(E)-octenyl)-2-methylbicyclo[3.3.1]non-2-en-9-yl]-[syn]-(+/-)-5-(Z)-heptenoate, methyl 7-[-5-(hydroxy-1-(E)-octenyl)-2,2-dimethylbicyclo[3.3.1]non-9-yl]-[syn]-(-+)-5-(Z)-heptenoate and methyl 7-[-5-(3-hydroxy-l-(E)-octenyl)-2,2-dimethylbicyclo[3.2.1]oct-8-yl]-[syn]-(-)-(Z)-heptenoate from a common functionalised bicycloalkane. During the synthesis of these functionalised bicycloalkanes several unexpected products were observed. These included the formation of methyl 5-methyl-6-oxa-7-oxobicyclo[3.2.2]-nonanecarboxylate during the sulphuric acid catalysed cyclisation of methyl 2-oxo-l-(3'-oxobutyl)cyclopentane-carboxylate which was contrary to the work of W G Dauben and J W McFarland and the formation of ethyl 4-methyl-bicyclo[4.4.0]dec-4,6-dienecarboxylate from the treatment of ethyl 1-(3'-methylbut-2'-ene)-2oxocyclohexanecarboxylate with stannic chloride. Another interesting rearrangement reaction was the formation of methyl 2-methine-5-oxohexanoate as well as methyl 4-oxo-3-(3'-oxobutyl)-3-tetrahydrothio-phenecarboxylate during the Michael reaction of methyl vinyl ketone with methyl 4-oxo-3-tetrahydrothiophene-carboxylate. Methyl 2-(2-methylbut-3'-en-2-yl)-3-oxo-tetrahydrothiophenecarboxylate was also an unexpected product from the alkylation of methyl 3-oxo-tetrahydrothio-phenecarboxylate with l-bromo-3-methylbut-2-ene."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis of thromboxane A2 analogues."]}]}],"canonical_facts":{"dc:creator":["Evans, Elizabeth Hannah."],"dc:date":["1984"],"dc:date.issued":["1984"],"dc:description.abstract":["The aim of the project was to synthesize novel thromboxane A2 analogues which would be potential thromboxane A2 antagonists. Three thromboxane A2 analogues were synthesized, methyl 7-[-5-(3-hydroxy-1-(E)-octenyl)-2-methylbicyclo[3.3.1]non-2-en-9-yl]-[syn]-(+/-)-5-(Z)-heptenoate, methyl 7-[-5-(hydroxy-1-(E)-octenyl)-2,2-dimethylbicyclo[3.3.1]non-9-yl]-[syn]-(-+)-5-(Z)-heptenoate and methyl 7-[-5-(3-hydroxy-l-(E)-octenyl)-2,2-dimethylbicyclo[3.2.1]oct-8-yl]-[syn]-(-)-(Z)-heptenoate from a common functionalised bicycloalkane. During the synthesis of these functionalised bicycloalkanes several unexpected products were observed. These included the formation of methyl 5-methyl-6-oxa-7-oxobicyclo[3.2.2]-nonanecarboxylate during the sulphuric acid catalysed cyclisation of methyl 2-oxo-l-(3'-oxobutyl)cyclopentane-carboxylate which was contrary to the work of W G Dauben and J W McFarland and the formation of ethyl 4-methyl-bicyclo[4.4.0]dec-4,6-dienecarboxylate from the treatment of ethyl 1-(3'-methylbut-2'-ene)-2oxocyclohexanecarboxylate with stannic chloride. Another interesting rearrangement reaction was the formation of methyl 2-methine-5-oxohexanoate as well as methyl 4-oxo-3-(3'-oxobutyl)-3-tetrahydrothio-phenecarboxylate during the Michael reaction of methyl vinyl ketone with methyl 4-oxo-3-tetrahydrothiophene-carboxylate. Methyl 2-(2-methylbut-3'-en-2-yl)-3-oxo-tetrahydrothiophenecarboxylate was also an unexpected product from the alkylation of methyl 3-oxo-tetrahydrothio-phenecarboxylate with l-bromo-3-methylbut-2-ene."],"dc:format":["application/pdf"],"dc:identifier.uri":["https://shura.shu.ac.uk/19630/1/10694511.pdf"],"dc:language":["en"],"dc:publisher.commercial":["Sheffield Hallam University,"],"dc:publisher.department":["Department of Chemistry."],"dc:publisher.institution":["Sheffield Hallam University (United Kingdom)."],"dc:relation.isreferencedby":["https://shura.shu.ac.uk/19630/"],"dc:title":["Synthesis of thromboxane A2 analogues."],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["phd"]},"updated_at":"2026-07-24T06:31:21Z"}