{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/89201"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/89201","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Chemical diversification of the natural products quinine, abietic acid and pleuromutilin by ring distortion","abstract":"Ring distortion reactions directly alter the core ring systems of small molecules and can lead to striking changes in molecular structure. Strategic application of ring distortion reactions to complex molecules, such as natural products, is an effective method for the generation of compounds that exhibit significant molecular complexity, but possess vastly different molecular structures. The compounds produced by this complexity to diversity approach are advantageous starting points for the discovery of new biologically active compounds, as they possess a level of molecular complexity found in approved drugs but lacking in other screening collections used in drug discovery. The chapters herein emphasize the utility of ring distortion reactions for modifying complex molecules and assert the potential of ring distortion as strategy for the synthesis of complex and diverse small molecules. Chapter 1 defines the different methods of ring distortion and demonstrates how these reactions can be employed for the selective modification of complex molecules. Chapter 2 focuses on the application of ring distortion reactions to the cinchona alkaloid natural product quinine towards the creation of a collection of complex and diverse small molecules. Chapter 3 details the ring distortion of the terpene natural product abietic acid and details strategies for the synthesis of derivative libraries from the products of ring distortion. Chapter 4 describes on the ring distortion of the terpene natural product pleuromutilin and the discovery of a pleuromutilin-derived compound with anticancer activity.","abstract_html":"Ring distortion reactions directly alter the core ring systems of small molecules and can lead to striking changes in molecular structure. Strategic application of ring distortion reactions to complex molecules, such as natural products, is an effective method for the generation of compounds that exhibit significant molecular complexity, but possess vastly different molecular structures. The compounds produced by this complexity to diversity approach are advantageous starting points for the discovery of new biologically active compounds, as they possess a level of molecular complexity found in approved drugs but lacking in other screening collections used in drug discovery. The chapters herein emphasize the utility of ring distortion reactions for modifying complex molecules and assert the potential of ring distortion as strategy for the synthesis of complex and diverse small molecules. Chapter 1 defines the different methods of ring distortion and demonstrates how these reactions can be employed for the selective modification of complex molecules. Chapter 2 focuses on the application of ring distortion reactions to the cinchona alkaloid natural product quinine towards the creation of a collection of complex and diverse small molecules. Chapter 3 details the ring distortion of the terpene natural product abietic acid and details strategies for the synthesis of derivative libraries from the products of ring distortion. Chapter 4 describes on the ring distortion of the terpene natural product pleuromutilin and the discovery of a pleuromutilin-derived compound with anticancer activity.","abstract_has_math":false,"creators":["Hicklin, Robert W"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Hergenrother, Paul J","Moore, Jeffrey S","White, M. Christina","Bailey, Ryan C"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2016,"date_issued":"2016-03-02T21:06:31Z","date_published":"2016-03-02T21:06:31Z","updated_at":"2026-07-22T22:26:32Z","subjects":["Ring Distortion","Natural Products","Organic Synthesis","Quinine","Abietic Acid","Pleuromutlin","Fenestrane"],"languages":["en"],"rights":["Copyright 2015 Robert Hicklin"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/89201","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Hergenrother, Paul J","Moore, Jeffrey S","White, M. 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Strategic application of ring distortion reactions to complex molecules, such as natural products, is an effective method for the generation of compounds that exhibit significant molecular complexity, but possess vastly different molecular structures. The compounds produced by this complexity to diversity approach are advantageous starting points for the discovery of new biologically active compounds, as they possess a level of molecular complexity found in approved drugs but lacking in other screening collections used in drug discovery. The chapters herein emphasize the utility of ring distortion reactions for modifying complex molecules and assert the potential of ring distortion as strategy for the synthesis of complex and diverse small molecules. Chapter 1 defines the different methods of ring distortion and demonstrates how these reactions can be employed for the selective modification of complex molecules. Chapter 2 focuses on the application of ring distortion reactions to the cinchona alkaloid natural product quinine towards the creation of a collection of complex and diverse small molecules. Chapter 3 details the ring distortion of the terpene natural product abietic acid and details strategies for the synthesis of derivative libraries from the products of ring distortion. Chapter 4 describes on the ring distortion of the terpene natural product pleuromutilin and the discovery of a pleuromutilin-derived compound with anticancer activity.","Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2017-12-01","The student, Robert Hicklin, accepted the attached license on 2015-11-16 at 12:50.","The student, Robert Hicklin, submitted this Dissertation for approval on 2015-11-16 at 13:04.","This Dissertation was approved for publication on 2015-11-18 at 08:42.","DSpace SAF Submission Ingestion Package generated from Vireo submission #8791 on 2016-03-02 at 14:13:08","Made available in DSpace on 2016-03-02T21:06:31Z (GMT). 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Christina","Bailey, Ryan C"],"dc:creator":["Hicklin, Robert W"],"dc:date":["2016-03-02T21:06:31Z","2018-03-03T10:15:25Z","2015-11-18","2015-12"],"dc:description":["Ring distortion reactions directly alter the core ring systems of small molecules and can lead to striking changes in molecular structure. Strategic application of ring distortion reactions to complex molecules, such as natural products, is an effective method for the generation of compounds that exhibit significant molecular complexity, but possess vastly different molecular structures. The compounds produced by this complexity to diversity approach are advantageous starting points for the discovery of new biologically active compounds, as they possess a level of molecular complexity found in approved drugs but lacking in other screening collections used in drug discovery. The chapters herein emphasize the utility of ring distortion reactions for modifying complex molecules and assert the potential of ring distortion as strategy for the synthesis of complex and diverse small molecules. Chapter 1 defines the different methods of ring distortion and demonstrates how these reactions can be employed for the selective modification of complex molecules. Chapter 2 focuses on the application of ring distortion reactions to the cinchona alkaloid natural product quinine towards the creation of a collection of complex and diverse small molecules. Chapter 3 details the ring distortion of the terpene natural product abietic acid and details strategies for the synthesis of derivative libraries from the products of ring distortion. Chapter 4 describes on the ring distortion of the terpene natural product pleuromutilin and the discovery of a pleuromutilin-derived compound with anticancer activity.","Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2017-12-01","The student, Robert Hicklin, accepted the attached license on 2015-11-16 at 12:50.","The student, Robert Hicklin, submitted this Dissertation for approval on 2015-11-16 at 13:04.","This Dissertation was approved for publication on 2015-11-18 at 08:42.","DSpace SAF Submission Ingestion Package generated from Vireo submission #8791 on 2016-03-02 at 14:13:08","Made available in DSpace on 2016-03-02T21:06:31Z (GMT). No. of bitstreams: 2 HICKLIN-DISSERTATION-2015.pdf: 17371504 bytes, checksum: 62a26a05e6ef7ace43589c0da7828fc2 (MD5) LICENSE.txt: 4211 bytes, checksum: 51c7774b3ffea3dd248495ac27b8ba26 (MD5) Previous issue date: 2015-11-18","Embargo set by: Seth Robbins for item 91404 Lift date: 2018-03-02T21:07:27Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system","Limited Restriction Lifted for Item 91404 on 2018-03-03T10:15:25Z."],"dc:format":["application/pdf"],"dc:identifier":["http://hdl.handle.net/2142/89201"],"dc:language":["en"],"dc:rights":["Copyright 2015 Robert Hicklin"],"dc:subject":["Ring Distortion","Natural Products","Organic Synthesis","Quinine","Abietic Acid","Pleuromutlin","Fenestrane"],"dc:title":["Chemical diversification of the natural products quinine, abietic acid and pleuromutilin by ring distortion"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:32Z"}