{"id":{"repo_id":"columbia-diss","oai_identifier":"oai:academiccommons.columbia.edu:10.7916/D8DN4C1T"},"canonical_url":"https://search.dev.ndltd.org/etd/columbia-diss/oai:academiccommons.columbia.edu:10.7916/D8DN4C1T","repository":{"repo_id":"columbia-diss","name":"Columbia University","base_url":"https://academiccommons.columbia.edu/oai"},"display":{"title":"Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies towards (+)-Cortistatin A","abstract":"The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A.","abstract_html":"The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A.","abstract_has_math":false,"creators":["Wang, Zhang"],"institution":null,"degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2011,"date_issued":"2011","date_published":"2011","updated_at":"2026-07-24T01:44:14Z","subjects":["Chemistry","Tricholoma","Diterpenes--Synthesis"],"languages":["English"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://doi.org/10.7916/D8DN4C1T","outbound_label":"DOI","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Wang, Zhang"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011"]},{"key":"dc:type","label":"Dc Type","values":["Theses"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Tricholoma","Diterpenes--Synthesis"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["English"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://doi.org/10.7916/D8DN4C1T"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A."]},{"key":"dc:title","label":"Title","values":["Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies towards (+)-Cortistatin A"]}]}],"canonical_facts":{"dc:creator":["Wang, Zhang"],"dc:date":["2011"],"dc:description":["The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A."],"dc:identifier":["https://doi.org/10.7916/D8DN4C1T"],"dc:language":["English"],"dc:subject":["Chemistry","Tricholoma","Diterpenes--Synthesis"],"dc:title":["Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies towards (+)-Cortistatin A"],"dc:type":["Theses"]},"updated_at":"2026-07-24T01:44:14Z"}