With intrinsic versatility and an overwhelming presence in natural products, nitrogen- and oxygen-containing heterocycles boast a plethora of medicinal properties. Specifically, lactams and lactones are the respective luminaries of the antibiotic and flavor worlds. However, the synthesis of fused lactams-lactones, especially those bearing trans-fusion, is challenging from the standpoints of chemoselectivity, stereoselectivity, and regioselectivity. In this thesis, the highly-selective, cost-effective, and high-yielding conversion of readily affordable allylic lactams into trans-fused lactam-lactones by intramolecular vicinal difunctionalization is explored. The approach is highly divergent and requires only two steps, which bodes well for the construction of medicinally pertinent fragments. It is anticipated that the aforementioned merits of the methodology will endear it to both the medicinal and synthesis communities.
","abstract_html":"<p>With intrinsic versatility and an overwhelming presence in natural products, nitrogen- and oxygen-containing heterocycles boast a plethora of medicinal properties. Specifically, lactams and lactones are the respective luminaries of the antibiotic and flavor worlds. However, the synthesis of fused lactams-lactones, especially those bearing <em>trans</em>-fusion, is challenging from the standpoints of chemoselectivity, stereoselectivity, and regioselectivity. In this thesis, the highly-selective, cost-effective, and high-yielding conversion of readily affordable allylic lactams into <em>trans</em>-fused lactam-lactones by intramolecular vicinal difunctionalization is explored. The approach is highly divergent and requires only two steps, which bodes well for the construction of medicinally pertinent fragments. It is anticipated that the aforementioned merits of the methodology will endear it to both the medicinal and synthesis communities.</p>","abstract_has_math":false,"creators":["Rodriguez, Morgan J."],"institution":null,"degree_name":"Master of Science (MS)","degree_level":null,"degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Timothy K. Beng","Levente Fabry-Asztalos","Carin Thomas-Bradley"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2020,"date_issued":"2020-01-01T08:00:00Z","date_published":"2020-01-01T08:00:00Z","updated_at":"2026-07-24T01:37:54Z","subjects":["Halolactonization","Castagnoli-Cushman","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.cwu.edu/etd/1443","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Timothy K. Beng","Levente Fabry-Asztalos","Carin Thomas-Bradley"]},{"key":"dc:creator","label":"Author","values":["Rodriguez, Morgan J."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2022-12-16T08:00:00Z"]},{"key":"dc:type","label":"Dc Type","values":["Text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MS)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Halolactonization","Castagnoli-Cushman","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://digitalcommons.cwu.edu/etd/1443"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["With intrinsic versatility and an overwhelming presence in natural products, nitrogen- and oxygen-containing heterocycles boast a plethora of medicinal properties. Specifically, lactams and lactones are the respective luminaries of the antibiotic and flavor worlds. However, the synthesis of fused lactams-lactones, especially those bearing trans-fusion, is challenging from the standpoints of chemoselectivity, stereoselectivity, and regioselectivity. In this thesis, the highly-selective, cost-effective, and high-yielding conversion of readily affordable allylic lactams into trans-fused lactam-lactones by intramolecular vicinal difunctionalization is explored. The approach is highly divergent and requires only two steps, which bodes well for the construction of medicinally pertinent fragments. It is anticipated that the aforementioned merits of the methodology will endear it to both the medicinal and synthesis communities.
"]},{"key":"dc:title","label":"Title","values":["Selective Synthesis of Trans-fused Lactam-Lactones by Vicinal Difunctionalization of Readily Affordable Allylic Lactams"]}]}],"canonical_facts":{"dc:contributor":["Timothy K. Beng","Levente Fabry-Asztalos","Carin Thomas-Bradley"],"dc:creator":["Rodriguez, Morgan J."],"dc:date.available":["2022-12-16T08:00:00Z"],"dc:description.abstract":["With intrinsic versatility and an overwhelming presence in natural products, nitrogen- and oxygen-containing heterocycles boast a plethora of medicinal properties. Specifically, lactams and lactones are the respective luminaries of the antibiotic and flavor worlds. However, the synthesis of fused lactams-lactones, especially those bearing trans-fusion, is challenging from the standpoints of chemoselectivity, stereoselectivity, and regioselectivity. In this thesis, the highly-selective, cost-effective, and high-yielding conversion of readily affordable allylic lactams into trans-fused lactam-lactones by intramolecular vicinal difunctionalization is explored. The approach is highly divergent and requires only two steps, which bodes well for the construction of medicinally pertinent fragments. It is anticipated that the aforementioned merits of the methodology will endear it to both the medicinal and synthesis communities.
"],"dc:identifier":["https://digitalcommons.cwu.edu/etd/1443"],"dc:subject":["Halolactonization","Castagnoli-Cushman","Organic Chemistry"],"dc:title":["Selective Synthesis of Trans-fused Lactam-Lactones by Vicinal Difunctionalization of Readily Affordable Allylic Lactams"],"dc:type":["Text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T01:37:54Z"}