{"id":{"repo_id":"uab","oai_identifier":"oai:digitalcommons.library.uab.edu:etd-collection-8080"},"canonical_url":"https://search.dev.ndltd.org/etd/uab/oai:digitalcommons.library.uab.edu:etd-collection-8080","repository":{"repo_id":"uab","name":"University of Alabama Birmingham","base_url":"https://digitalcommons.library.uab.edu/do/oai/"},"display":{"title":"The Synthesis of C-aryl-18-nor-steroids From Resin Acids and Their Derivatives.","abstract":"Our interest in the conversion of a resin acid to a C-aryl-18-nor-steroid was to see if this class of compounds could compete as starting materials in the medicinal chemistry field. Since resin acid derivatives are rather inexpensive compared to steroid systems, the economics seemed attractive.In order to cyclize a ring D onto the resin acid skeleton, it was important to convert the isopropyl group to an acetyl group. To achieve this goal, the Tahara modification of the Sanderson oxidation of dehydroabietonitrile was applied, to yield the 7-oxo-13-acetyl dehydroabietonitrile and the 7-oxo-13-isopropenyl derivative.Treating the diketone with formaldehyde and dimethylamine hydro-chloride, yielded the Mannich base, which with methyl-iodide formed the methiodide salt plus the vinyl-phenyl-ketone derivative.Cyclization of the vinyl product by means of a melt of aluminum chloride sodium chloride gave the desired steroid as the sole product.","abstract_html":"Our interest in the conversion of a resin acid to a C-aryl-18-nor-steroid was to see if this class of compounds could compete as starting materials in the medicinal chemistry field. Since resin acid derivatives are rather inexpensive compared to steroid systems, the economics seemed attractive.In order to cyclize a ring D onto the resin acid skeleton, it was important to convert the isopropyl group to an acetyl group. To achieve this goal, the Tahara modification of the Sanderson oxidation of dehydroabietonitrile was applied, to yield the 7-oxo-13-acetyl dehydroabietonitrile and the 7-oxo-13-isopropenyl derivative.Treating the diketone with formaldehyde and dimethylamine hydro-chloride, yielded the Mannich base, which with methyl-iodide formed the methiodide salt plus the vinyl-phenyl-ketone derivative.Cyclization of the vinyl product by means of a melt of aluminum chloride sodium chloride gave the desired steroid as the sole product.","abstract_has_math":false,"creators":["Gawish, Ali Abd El-Salam"],"institution":null,"degree_name":null,"degree_level":"Dissertation","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1979,"date_issued":"1979-01-01T08:00:00Z","date_published":"1979-01-01T08:00:00Z","updated_at":"2026-07-24T05:05:46Z","subjects":["C-aryl-18-nor-steroid","Resin acids","Medicinal chemistry","Sanderson oxidation"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.library.uab.edu/etd-collection/7088","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Gawish, Ali Abd El-Salam"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["C-aryl-18-nor-steroid","Resin acids","Medicinal chemistry","Sanderson oxidation"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://digitalcommons.library.uab.edu/etd-collection/7088"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Our interest in the conversion of a resin acid to a C-aryl-18-nor-steroid was to see if this class of compounds could compete as starting materials in the medicinal chemistry field. Since resin acid derivatives are rather inexpensive compared to steroid systems, the economics seemed attractive.In order to cyclize a ring D onto the resin acid skeleton, it was important to convert the isopropyl group to an acetyl group. To achieve this goal, the Tahara modification of the Sanderson oxidation of dehydroabietonitrile was applied, to yield the 7-oxo-13-acetyl dehydroabietonitrile and the 7-oxo-13-isopropenyl derivative.Treating the diketone with formaldehyde and dimethylamine hydro-chloride, yielded the Mannich base, which with methyl-iodide formed the methiodide salt plus the vinyl-phenyl-ketone derivative.Cyclization of the vinyl product by means of a melt of aluminum chloride sodium chloride gave the desired steroid as the sole product."]},{"key":"dc:title","label":"Title","values":["The Synthesis of C-aryl-18-nor-steroids From Resin Acids and Their Derivatives."]}]}],"canonical_facts":{"dc:creator":["Gawish, Ali Abd El-Salam"],"dc:description.abstract":["Our interest in the conversion of a resin acid to a C-aryl-18-nor-steroid was to see if this class of compounds could compete as starting materials in the medicinal chemistry field. Since resin acid derivatives are rather inexpensive compared to steroid systems, the economics seemed attractive.In order to cyclize a ring D onto the resin acid skeleton, it was important to convert the isopropyl group to an acetyl group. To achieve this goal, the Tahara modification of the Sanderson oxidation of dehydroabietonitrile was applied, to yield the 7-oxo-13-acetyl dehydroabietonitrile and the 7-oxo-13-isopropenyl derivative.Treating the diketone with formaldehyde and dimethylamine hydro-chloride, yielded the Mannich base, which with methyl-iodide formed the methiodide salt plus the vinyl-phenyl-ketone derivative.Cyclization of the vinyl product by means of a melt of aluminum chloride sodium chloride gave the desired steroid as the sole product."],"dc:identifier":["https://digitalcommons.library.uab.edu/etd-collection/7088"],"dc:subject":["C-aryl-18-nor-steroid","Resin acids","Medicinal chemistry","Sanderson oxidation"],"dc:title":["The Synthesis of C-aryl-18-nor-steroids From Resin Acids and Their Derivatives."],"thesis:degree_level":["Dissertation"]},"updated_at":"2026-07-24T05:05:46Z"}