{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/95520"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/95520","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Total synthesis of lycoricidine via photochemical dearomative dihydroxylation","abstract":"Lycoricidine a member of the amaryllidaceae isocarbostyril alkaloid family of natural products isolated from bulbs of plants in the amaryllidaceae family, which include the common daffodil. The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein. This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.","abstract_html":"Lycoricidine a member of the amaryllidaceae isocarbostyril alkaloid family of natural products isolated from bulbs of plants in the amaryllidaceae family, which include the common daffodil. The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein. This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.","abstract_has_math":false,"creators":["Holycross, Daniel Robert"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"M.S.","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Sarlah, David"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017-03-01T16:37:11Z","date_published":"2017-03-01T16:37:11Z","updated_at":"2026-07-22T22:26:37Z","subjects":["Lycoricidine","total synthesis","dearomative dihydroxylation"],"languages":["en"],"rights":["Copyright 2016 Daniel Holycross"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/95520","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Sarlah, David"]},{"key":"dc:creator","label":"Author","values":["Holycross, Daniel Robert"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2017-03-01T16:37:11Z","2019-03-02T10:15:30Z","2016-12-08","2016-12"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.S."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Lycoricidine","total synthesis","dearomative dihydroxylation"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2016 Daniel Holycross"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/95520"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Lycoricidine a member of the amaryllidaceae isocarbostyril alkaloid family of natural products isolated from bulbs of plants in the amaryllidaceae family, which include the common daffodil. The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein. This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2018-12-01","The student, Daniel Holycross, accepted the attached license on 2016-12-08 at 11:00.","The student, Daniel Holycross, submitted this Thesis for approval on 2016-12-08 at 11:15.","This Thesis was approved for publication on 2016-12-08 at 13:25.","DSpace SAF Submission Ingestion Package generated from Vireo submission #10486 on 2017-02-28 at 14:37:37","Made available in DSpace on 2017-03-01T16:37:11Z (GMT). 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The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein. This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.","Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2018-12-01","The student, Daniel Holycross, accepted the attached license on 2016-12-08 at 11:00.","The student, Daniel Holycross, submitted this Thesis for approval on 2016-12-08 at 11:15.","This Thesis was approved for publication on 2016-12-08 at 13:25.","DSpace SAF Submission Ingestion Package generated from Vireo submission #10486 on 2017-02-28 at 14:37:37","Made available in DSpace on 2017-03-01T16:37:11Z (GMT). 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