{"id":{"repo_id":"soton","oai_identifier":"oai:eprints.soton.ac.uk:173853"},"canonical_url":"https://search.dev.ndltd.org/etd/soton/oai:eprints.soton.ac.uk:173853","repository":{"repo_id":"soton","name":"University of Southampton","base_url":"https://eprints.soton.ac.uk/cgi/oai2"},"display":{"title":"Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins","abstract":"The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been<br/>completed. Notable steps included the alcoholytic kinetic resolution of epoxide<br/>2.2, two permanganate promoted oxidative cyclisation reactions, a tethered<br/>RCM to unite the two major fragments and the use of P4 phoshazene base to<br/>install the butenolide precursor.<br/><br/>Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative<br/>cyclisation reactions with permanganate is an attractive route to many<br/>Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF<br/>core and synthesis of an adjacent bis-THF core are discussed.","abstract_html":"The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been&lt;br/&gt;completed. Notable steps included the alcoholytic kinetic resolution of epoxide&lt;br/&gt;2.2, two permanganate promoted oxidative cyclisation reactions, a tethered&lt;br/&gt;RCM to unite the two major fragments and the use of P4 phoshazene base to&lt;br/&gt;install the butenolide precursor.&lt;br/&gt;&lt;br/&gt;Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative&lt;br/&gt;cyclisation reactions with permanganate is an attractive route to many&lt;br/&gt;Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF&lt;br/&gt;core and synthesis of an adjacent bis-THF core are discussed.","abstract_has_math":false,"creators":["Spurr, Ian Bruce"],"institution":"University of Southampton","degree_name":"Ph.D.","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Brown, Richard C.D."],"committee_chairs":[],"committee_members":[],"year":2010,"date_issued":"2010-06","date_published":"2010-06","updated_at":"2026-07-24T04:36:21Z","subjects":[],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Brown, Richard C.D."]},{"key":"dc:creator","label":"Author","values":["Spurr, Ian Bruce"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2010-06"]},{"key":"dc:date.issued","label":"Date","values":["2010-06"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Chemistry (pre 2011 reorg)","School of Chemistry"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Southampton"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://eprints.soton.ac.uk/173853/"]},{"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":["Ph.D."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://eprints.soton.ac.uk/173853/1/Thesis.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been<br/>completed. Notable steps included the alcoholytic kinetic resolution of epoxide<br/>2.2, two permanganate promoted oxidative cyclisation reactions, a tethered<br/>RCM to unite the two major fragments and the use of P4 phoshazene base to<br/>install the butenolide precursor.<br/><br/>Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative<br/>cyclisation reactions with permanganate is an attractive route to many<br/>Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF<br/>core and synthesis of an adjacent bis-THF core are discussed."]},{"key":"dc:format","label":"Dc Format","values":["text"]},{"key":"dc:title","label":"Title","values":["Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins"]}]}],"canonical_facts":{"dc:contributor.advisor":["Brown, Richard C.D."],"dc:creator":["Spurr, Ian Bruce"],"dc:date":["2010-06"],"dc:date.issued":["2010-06"],"dc:description.abstract":["The total synthesis of potent antitumour agent cis-sylvaticin (1.100) has been<br/>completed. Notable steps included the alcoholytic kinetic resolution of epoxide<br/>2.2, two permanganate promoted oxidative cyclisation reactions, a tethered<br/>RCM to unite the two major fragments and the use of P4 phoshazene base to<br/>install the butenolide precursor.<br/><br/>Synthesis of adjacent THP-THF and bis-THF cores via cascade oxidative<br/>cyclisation reactions with permanganate is an attractive route to many<br/>Annonaceous acetogenins. Attempted synthesis of an adjacent THP-THF<br/>core and synthesis of an adjacent bis-THF core are discussed."],"dc:format":["text"],"dc:identifier.uri":["https://eprints.soton.ac.uk/173853/1/Thesis.pdf"],"dc:publisher.department":["Chemistry (pre 2011 reorg)","School of Chemistry"],"dc:publisher.institution":["University of Southampton"],"dc:relation.isreferencedby":["https://eprints.soton.ac.uk/173853/"],"dc:title":["Total synthesis of cis-sylvaticin and synthetic studies towards the synthesis of adjacent THF-THF and THF-THP Annonaceous acetogenins"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["Ph.D."]},"updated_at":"2026-07-24T04:36:21Z"}