{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84468"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84468","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"The Enantiospecific Total Syntheses of Adda and Nodularin","abstract":"The unusual amino acid (2S, 3S, 4 E, 6E, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) is a structural component of nodularin that has been reported to be necessary for biological activity. The complexity of Adda has hindered the completion of structure activity relationship (SAR) studies. This work has focused on development of procedures to synthesize Adda. As a result, novel methodology has been developed and employed to synthesize N -Boc-Adda in 40% overall yield in a 13 step linear synthesis. A convergent synthesis of N-Boc Adda was developed that provided N-Boc-Adda in 31% overall yield after 16 steps. Both procedures supply the N-Boc-Adda in yields that are several times higher than the best syntheses from commercially available material reported to date. These procedures for the synthesis of N-Boc-Adda should facilitate development of SAR studies to elucidate roles of protein phosphatases in tumor promotion or suppression.","abstract_html":"The unusual amino acid (2S, 3S, 4 E, 6E, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) is a structural component of nodularin that has been reported to be necessary for biological activity. The complexity of Adda has hindered the completion of structure activity relationship (SAR) studies. This work has focused on development of procedures to synthesize Adda. As a result, novel methodology has been developed and employed to synthesize N -Boc-Adda in 40% overall yield in a 13 step linear synthesis. A convergent synthesis of N-Boc Adda was developed that provided N-Boc-Adda in 31% overall yield after 16 steps. Both procedures supply the N-Boc-Adda in yields that are several times higher than the best syntheses from commercially available material reported to date. These procedures for the synthesis of N-Boc-Adda should facilitate development of SAR studies to elucidate roles of protein phosphatases in tumor promotion or suppression.","abstract_has_math":false,"creators":["Pearson, Jason Clay"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Rinehart, Kenneth L., Jr."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:14:39Z","date_published":"2015-09-25T22:14:39Z","updated_at":"2026-07-22T22:26:23Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI9955655"],"render_values":[{"text":"(MiAaPQ)AAI9955655","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84468","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Rinehart, Kenneth L., Jr."]},{"key":"dc:creator","label":"Author","values":["Pearson, Jason Clay"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:14:39Z","10000-01-01","1999"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"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":["Chemistry, Organic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84468","(MiAaPQ)AAI9955655"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The unusual amino acid (2S, 3S, 4 E, 6E, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) is a structural component of nodularin that has been reported to be necessary for biological activity. The complexity of Adda has hindered the completion of structure activity relationship (SAR) studies. This work has focused on development of procedures to synthesize Adda. As a result, novel methodology has been developed and employed to synthesize N -Boc-Adda in 40% overall yield in a 13 step linear synthesis. A convergent synthesis of N-Boc Adda was developed that provided N-Boc-Adda in 31% overall yield after 16 steps. Both procedures supply the N-Boc-Adda in yields that are several times higher than the best syntheses from commercially available material reported to date. These procedures for the synthesis of N-Boc-Adda should facilitate development of SAR studies to elucidate roles of protein phosphatases in tumor promotion or suppression.","Made available in DSpace on 2015-09-25T22:14:39Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 9955655.pdf: 6864916 bytes, checksum: 3f0559f698f03bced4814b38ebfd1703 (MD5) Previous issue date: 1999","Embargo set by: Seth Robbins for item 85749 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","164 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1999."]},{"key":"dc:title","label":"Title","values":["The Enantiospecific Total Syntheses of Adda and Nodularin"]}]}],"canonical_facts":{"dc:contributor":["Rinehart, Kenneth L., Jr."],"dc:creator":["Pearson, Jason Clay"],"dc:date":["2015-09-25T22:14:39Z","10000-01-01","1999"],"dc:description":["The unusual amino acid (2S, 3S, 4 E, 6E, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) is a structural component of nodularin that has been reported to be necessary for biological activity. The complexity of Adda has hindered the completion of structure activity relationship (SAR) studies. This work has focused on development of procedures to synthesize Adda. As a result, novel methodology has been developed and employed to synthesize N -Boc-Adda in 40% overall yield in a 13 step linear synthesis. A convergent synthesis of N-Boc Adda was developed that provided N-Boc-Adda in 31% overall yield after 16 steps. Both procedures supply the N-Boc-Adda in yields that are several times higher than the best syntheses from commercially available material reported to date. These procedures for the synthesis of N-Boc-Adda should facilitate development of SAR studies to elucidate roles of protein phosphatases in tumor promotion or suppression.","Made available in DSpace on 2015-09-25T22:14:39Z (GMT). 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