{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/89043"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/89043","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents","abstract":"Trichodermamide B, isolated from the marine fungus Trichoderma virens in 2003, is a potent anti-cancer agent and with complex molecular architecture. It is hypothesized herein that this molecule may be derived in nature from phenylalanine via a benzene oxide intermediate. Utilizing a bioinspired strategy, synthetic studies towards trichodermamide B have been conducted utilizing arene oxide equivalents as key synthetic intermediates. Notable synthetic transformations include alkylation with a novel, α–bromo oximoester electrophile and allylic bromination of an advanced, spirocyclic intermediate. This strategy has enabled access to advanced intermediates and should afford the natural product in far fewer steps than previously reported syntheses of this compound. Once complete, this concise synthetic strategy should afford enough material to conduct mechanism of action studies to uncover the origin of trichodermamide B’s impressive biological activity.","abstract_html":"Trichodermamide B, isolated from the marine fungus Trichoderma virens in 2003, is a potent anti-cancer agent and with complex molecular architecture. It is hypothesized herein that this molecule may be derived in nature from phenylalanine via a benzene oxide intermediate. Utilizing a bioinspired strategy, synthetic studies towards trichodermamide B have been conducted utilizing arene oxide equivalents as key synthetic intermediates. Notable synthetic transformations include alkylation with a novel, α–bromo oximoester electrophile and allylic bromination of an advanced, spirocyclic intermediate. This strategy has enabled access to advanced intermediates and should afford the natural product in far fewer steps than previously reported syntheses of this compound. Once complete, this concise synthetic strategy should afford enough material to conduct mechanism of action studies to uncover the origin of trichodermamide B’s impressive biological activity.","abstract_has_math":false,"creators":["Reynolds, Bryan Joseph"],"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":2016,"date_issued":"2016-03-02T19:34:17Z","date_published":"2016-03-02T19:34:17Z","updated_at":"2026-07-22T22:26:32Z","subjects":["Trichodermamide B","arene oxide","dearomatization","alkylation","natural product","total synthesis","biomimetic"],"languages":["en"],"rights":["Copyright 2015 Bryan Reynolds"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/89043","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":["Reynolds, Bryan Joseph"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2016-03-02T19:34:17Z","2015-12-04","2015-12"]},{"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":["Trichodermamide B","arene oxide","dearomatization","alkylation","natural product","total synthesis","biomimetic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2015 Bryan Reynolds"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/89043"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Trichodermamide B, isolated from the marine fungus Trichoderma virens in 2003, is a potent anti-cancer agent and with complex molecular architecture. It is hypothesized herein that this molecule may be derived in nature from phenylalanine via a benzene oxide intermediate. Utilizing a bioinspired strategy, synthetic studies towards trichodermamide B have been conducted utilizing arene oxide equivalents as key synthetic intermediates. Notable synthetic transformations include alkylation with a novel, α–bromo oximoester electrophile and allylic bromination of an advanced, spirocyclic intermediate. This strategy has enabled access to advanced intermediates and should afford the natural product in far fewer steps than previously reported syntheses of this compound. Once complete, this concise synthetic strategy should afford enough material to conduct mechanism of action studies to uncover the origin of trichodermamide B’s impressive biological activity.","Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2016-03-02 without embargo terms","The student, Bryan Reynolds, accepted the attached license on 2015-12-02 at 17:34.","The student, Bryan Reynolds, submitted this Thesis for approval on 2015-12-02 at 17:40.","This Thesis was approved for publication on 2015-12-04 at 12:02.","DSpace SAF Submission Ingestion Package generated from Vireo submission #8913 on 2016-03-02 at 12:51:18","Made available in DSpace on 2016-03-02T19:34:17Z (GMT). No. of bitstreams: 2 REYNOLDS-THESIS-2015.pdf: 2718829 bytes, checksum: 4dc871936dbacb7ee0ba1f6a65169298 (MD5) LICENSE.txt: 4211 bytes, checksum: b30f6e21ee30c479ed6135048b5bc0e2 (MD5) Previous issue date: 2015-12-04"]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthetic studies towards trichodermamide B: expedient synthesis enabled by arene oxide equivalents"]}]}],"canonical_facts":{"dc:contributor":["Sarlah, David"],"dc:creator":["Reynolds, Bryan Joseph"],"dc:date":["2016-03-02T19:34:17Z","2015-12-04","2015-12"],"dc:description":["Trichodermamide B, isolated from the marine fungus Trichoderma virens in 2003, is a potent anti-cancer agent and with complex molecular architecture. It is hypothesized herein that this molecule may be derived in nature from phenylalanine via a benzene oxide intermediate. Utilizing a bioinspired strategy, synthetic studies towards trichodermamide B have been conducted utilizing arene oxide equivalents as key synthetic intermediates. Notable synthetic transformations include alkylation with a novel, α–bromo oximoester electrophile and allylic bromination of an advanced, spirocyclic intermediate. This strategy has enabled access to advanced intermediates and should afford the natural product in far fewer steps than previously reported syntheses of this compound. Once complete, this concise synthetic strategy should afford enough material to conduct mechanism of action studies to uncover the origin of trichodermamide B’s impressive biological activity.","Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2016-03-02 without embargo terms","The student, Bryan Reynolds, accepted the attached license on 2015-12-02 at 17:34.","The student, Bryan Reynolds, submitted this Thesis for approval on 2015-12-02 at 17:40.","This Thesis was approved for publication on 2015-12-04 at 12:02.","DSpace SAF Submission Ingestion Package generated from Vireo submission #8913 on 2016-03-02 at 12:51:18","Made available in DSpace on 2016-03-02T19:34:17Z (GMT). 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