{"id":{"repo_id":"houston","oai_identifier":"oai:uh-ir.tdl.org:10657/6552"},"canonical_url":"https://search.dev.ndltd.org/etd/houston/oai:uh-ir.tdl.org:10657/6552","repository":{"repo_id":"houston","name":"University of Houston","base_url":"https://uh-ir.tdl.org/server/oai/request"},"display":{"title":"Synthesis of the Antimalarial Flindersial Alkaloids","abstract":"The concept of mimicking nature to synthesize natural compounds has been successfully demonstrated in the synthesis of all the anti-malarial Flindersia alkaloids. Previous work on the biosynthesis of the related natural products borreverine and isoborreverine inspired us to synthesize racemic flinderoles A, B, and C in as few as three synthetic steps from simple and readily available materials. The development of reaction conditions for the dimerization of borrerine in the presence of acid is discussed in detail. The progress toward the enantioselective total synthesis of flinderoles A, B, and C is also presented. The retrosynthetic plan was inspired by the biomimetic synthesis of the flinderoles, in which an acid mediated amino cyclization would form the flinderole framework. Tryptamine and 3-butyn-2-one undergo a vinylogous Pictet-Spengler reaction to give a β-carboline, which opens to a 2-enone tryptamine in the presence of base. A BINOL catalyzed enantioselective conjugate addition of a vinyl boronic acid to the 2-enone tryptamine has been achieved. A pyrrolo[a]indole unit could be connected to another indole unit by a Sonagashira coupling reaction in a convergent manner.","abstract_html":"The concept of mimicking nature to synthesize natural compounds has been successfully demonstrated in the synthesis of all the anti-malarial Flindersia alkaloids. Previous work on the biosynthesis of the related natural products borreverine and isoborreverine inspired us to synthesize racemic flinderoles A, B, and C in as few as three synthetic steps from simple and readily available materials. The development of reaction conditions for the dimerization of borrerine in the presence of acid is discussed in detail. The progress toward the enantioselective total synthesis of flinderoles A, B, and C is also presented. The retrosynthetic plan was inspired by the biomimetic synthesis of the flinderoles, in which an acid mediated amino cyclization would form the flinderole framework. Tryptamine and 3-butyn-2-one undergo a vinylogous Pictet-Spengler reaction to give a β-carboline, which opens to a 2-enone tryptamine in the presence of base. A BINOL catalyzed enantioselective conjugate addition of a vinyl boronic acid to the 2-enone tryptamine has been achieved. A pyrrolo[a]indole unit could be connected to another indole unit by a Sonagashira coupling reaction in a convergent manner.","abstract_has_math":false,"creators":["Vallakati, Ravikrishna 1977-"],"institution":"University of Houston","degree_name":"Doctor of Philosophy","degree_level":"Doctoral","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["May, Jeremy A."],"committee_chairs":[],"committee_members":["Gilbertson, Scott R.","Thummel, Randolph P.","Cuny, Gregory D.","Xu, Shoujun"],"year":2015,"date_issued":"2015-05","date_published":"2015-05","updated_at":"2026-07-24T02:32:54Z","subjects":["Flinderoles, antimalarial, Biomimetic Synthesis, Organocatalysis"],"languages":["eng"],"rights":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. UH Libraries has secured permission to reproduce any and all previously published materials contained in the work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10657/6552","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["May, Jeremy A."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Gilbertson, Scott R.","Thummel, Randolph P.","Cuny, Gregory D.","Xu, Shoujun"]},{"key":"dc:creator","label":"Author","values":["Vallakati, Ravikrishna 1977-"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2020-06-02T02:17:57Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2020-06-02T02:17:57Z"]},{"key":"dc:date.issued","label":"Date","values":["2015-05"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Houston"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Flinderoles, antimalarial, Biomimetic Synthesis, Organocatalysis"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. UH Libraries has secured permission to reproduce any and all previously published materials contained in the work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/10657/6552"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The concept of mimicking nature to synthesize natural compounds has been successfully demonstrated in the synthesis of all the anti-malarial Flindersia alkaloids. Previous work on the biosynthesis of the related natural products borreverine and isoborreverine inspired us to synthesize racemic flinderoles A, B, and C in as few as three synthetic steps from simple and readily available materials. The development of reaction conditions for the dimerization of borrerine in the presence of acid is discussed in detail. The progress toward the enantioselective total synthesis of flinderoles A, B, and C is also presented. The retrosynthetic plan was inspired by the biomimetic synthesis of the flinderoles, in which an acid mediated amino cyclization would form the flinderole framework. Tryptamine and 3-butyn-2-one undergo a vinylogous Pictet-Spengler reaction to give a β-carboline, which opens to a 2-enone tryptamine in the presence of base. A BINOL catalyzed enantioselective conjugate addition of a vinyl boronic acid to the 2-enone tryptamine has been achieved. A pyrrolo[a]indole unit could be connected to another indole unit by a Sonagashira coupling reaction in a convergent manner."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis of the Antimalarial Flindersial Alkaloids"]}]}],"canonical_facts":{"dc:contributor.advisor":["May, Jeremy A."],"dc:contributor.committeemember":["Gilbertson, Scott R.","Thummel, Randolph P.","Cuny, Gregory D.","Xu, Shoujun"],"dc:creator":["Vallakati, Ravikrishna 1977-"],"dc:date.accessioned":["2020-06-02T02:17:57Z"],"dc:date.available":["2020-06-02T02:17:57Z"],"dc:date.issued":["2015-05"],"dc:description.abstract":["The concept of mimicking nature to synthesize natural compounds has been successfully demonstrated in the synthesis of all the anti-malarial Flindersia alkaloids. Previous work on the biosynthesis of the related natural products borreverine and isoborreverine inspired us to synthesize racemic flinderoles A, B, and C in as few as three synthetic steps from simple and readily available materials. The development of reaction conditions for the dimerization of borrerine in the presence of acid is discussed in detail. The progress toward the enantioselective total synthesis of flinderoles A, B, and C is also presented. The retrosynthetic plan was inspired by the biomimetic synthesis of the flinderoles, in which an acid mediated amino cyclization would form the flinderole framework. Tryptamine and 3-butyn-2-one undergo a vinylogous Pictet-Spengler reaction to give a β-carboline, which opens to a 2-enone tryptamine in the presence of base. A BINOL catalyzed enantioselective conjugate addition of a vinyl boronic acid to the 2-enone tryptamine has been achieved. A pyrrolo[a]indole unit could be connected to another indole unit by a Sonagashira coupling reaction in a convergent manner."],"dc:format.mimetype":["application/pdf"],"dc:identifier.uri":["https://hdl.handle.net/10657/6552"],"dc:language.iso":["eng"],"dc:rights":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. UH Libraries has secured permission to reproduce any and all previously published materials contained in the work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."],"dc:subject":["Flinderoles, antimalarial, Biomimetic Synthesis, Organocatalysis"],"dc:title":["Synthesis of the Antimalarial Flindersial Alkaloids"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Doctoral"],"thesis:degree_name":["Doctor of Philosophy"],"thesis:institution_name":["University of Houston"]},"updated_at":"2026-07-24T02:32:54Z"}