{"id":{"repo_id":"soton","oai_identifier":"oai:eprints.soton.ac.uk:191321"},"canonical_url":"https://search.dev.ndltd.org/etd/soton/oai:eprints.soton.ac.uk:191321","repository":{"repo_id":"soton","name":"University of Southampton","base_url":"https://eprints.soton.ac.uk/cgi/oai2"},"display":{"title":"A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel","abstract":"Proposed are the total syntheses of the steroids desogestrel and estrone, utilizing a 1,4 addition/alkylation process to install the correct stereochemistry at C8, C13 and C14 in a single-pot operation. The racemic total synthesis of desogestrel includes a successful domino anionic cyclisation leading to the formation of the steroid C and B rings in a single operation with complete stereocontrol at C9. The ?-keto phosphonates obtained were subsequently subjected to A-ring annelation via a multistep one-pot process. The enantioselective synthesis as well as the racemic total synthesis of estrone include a sequential C and B-ring formation through ring closing metathesis and intramolecular Heck reaction","abstract_html":"Proposed are the total syntheses of the steroids desogestrel and estrone, utilizing a 1,4 addition/alkylation process to install the correct stereochemistry at C8, C13 and C14 in a single-pot operation. The racemic total synthesis of desogestrel includes a successful domino anionic cyclisation leading to the formation of the steroid C and B rings in a single operation with complete stereocontrol at C9. The ?-keto phosphonates obtained were subsequently subjected to A-ring annelation via a multistep one-pot process. The enantioselective synthesis as well as the racemic total synthesis of estrone include a sequential C and B-ring formation through ring closing metathesis and intramolecular Heck reaction","abstract_has_math":false,"creators":["Foucher, Vincent"],"institution":"University of Southampton","degree_name":"Ph.D.","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Linclau, Bruno"],"committee_chairs":[],"committee_members":[],"year":2010,"date_issued":"2010-08","date_published":"2010-08","updated_at":"2026-07-24T04:36:25Z","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":["Linclau, Bruno"]},{"key":"dc:creator","label":"Author","values":["Foucher, Vincent"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2010-08-27"]},{"key":"dc:date.issued","label":"Date","values":["2010-08"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Chemistry (pre 2011 reorg)","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/191321/"]},{"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/191321/1/ThesisVincent_CORRECTED.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Proposed are the total syntheses of the steroids desogestrel and estrone, utilizing a 1,4 addition/alkylation process to install the correct stereochemistry at C8, C13 and C14 in a single-pot operation. The racemic total synthesis of desogestrel includes a successful domino anionic cyclisation leading to the formation of the steroid C and B rings in a single operation with complete stereocontrol at C9. The ?-keto phosphonates obtained were subsequently subjected to A-ring annelation via a multistep one-pot process. The enantioselective synthesis as well as the racemic total synthesis of estrone include a sequential C and B-ring formation through ring closing metathesis and intramolecular Heck reaction"]},{"key":"dc:format","label":"Dc Format","values":["text"]},{"key":"dc:title","label":"Title","values":["A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel"]}]}],"canonical_facts":{"dc:contributor.advisor":["Linclau, Bruno"],"dc:creator":["Foucher, Vincent"],"dc:date":["2010-08-27"],"dc:date.issued":["2010-08"],"dc:description.abstract":["Proposed are the total syntheses of the steroids desogestrel and estrone, utilizing a 1,4 addition/alkylation process to install the correct stereochemistry at C8, C13 and C14 in a single-pot operation. The racemic total synthesis of desogestrel includes a successful domino anionic cyclisation leading to the formation of the steroid C and B rings in a single operation with complete stereocontrol at C9. The ?-keto phosphonates obtained were subsequently subjected to A-ring annelation via a multistep one-pot process. The enantioselective synthesis as well as the racemic total synthesis of estrone include a sequential C and B-ring formation through ring closing metathesis and intramolecular Heck reaction"],"dc:format":["text"],"dc:identifier.uri":["https://eprints.soton.ac.uk/191321/1/ThesisVincent_CORRECTED.pdf"],"dc:publisher.department":["Chemistry (pre 2011 reorg)","Chemistry"],"dc:publisher.institution":["University of Southampton"],"dc:relation.isreferencedby":["https://eprints.soton.ac.uk/191321/"],"dc:title":["A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["Ph.D."]},"updated_at":"2026-07-24T04:36:25Z"}