{"id":{"repo_id":"vilnius","oai_identifier":"oai:vu.lt:elaba:20203840"},"canonical_url":"https://search.dev.ndltd.org/etd/vilnius/oai:vu.lt:elaba:20203840","repository":{"repo_id":"vilnius","name":"Vilnius University","base_url":"https://epublications.vu.lt/oai"},"display":{"title":"Optimalios sarpaginų šeimos alkaloidų sintezės paieška /","abstract":"To date, the Pictet−Spengler reaction of tryptophan derivatives remains a key strategic transformation for the stereospecific synthesis of macroline, sarpagine and ajmaline related indole alkaloids. As a consequence, the synthesis of congeners possessing oxygenated indole ring requires the optimization of enantioselective routes to the relevant oxygenated tryptophan analogues.By contrast, the potential of the 9-azabicyclo[3.3.1]nonane synthons for de novo construction of the indole moiety of cycloocta[b]indole core is considerably less explored. In this work, a generalized synthetic access to Sarpagine alkaloids through a new synthon based on 9-azabicyclo[3.3.1]nonane core is presented. Synthesis of a new precursor was accomplished in four steps enantioselectively and without protecting groups. Fischer indolization reaction to forge the natural product’s carbon framework was also investigated, which provided an access to Sarpagine related alkaloids and their synthetic analogues.","abstract_html":"To date, the Pictet−Spengler reaction of tryptophan derivatives remains a key strategic transformation for the stereospecific synthesis of macroline, sarpagine and ajmaline related indole alkaloids. As a consequence, the synthesis of congeners possessing oxygenated indole ring requires the optimization of enantioselective routes to the relevant oxygenated tryptophan analogues.By contrast, the potential of the 9-azabicyclo[3.3.1]nonane synthons for de novo construction of the indole moiety of cycloocta[b]indole core is considerably less explored. In this work, a generalized synthetic access to Sarpagine alkaloids through a new synthon based on 9-azabicyclo[3.3.1]nonane core is presented. Synthesis of a new precursor was accomplished in four steps enantioselectively and without protecting groups. Fischer indolization reaction to forge the natural product’s carbon framework was also investigated, which provided an access to Sarpagine related alkaloids and their synthetic analogues.","abstract_has_math":false,"creators":["Gegevičius, Rokas,"],"institution":"Institutional Repository of Vilnius University","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Orentas, Edvinas"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2016,"date_issued":"2016","date_published":"2016","updated_at":"2026-07-24T05:55:44Z","subjects":[],"languages":["lit"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://repository.vu.lt/VU:ELABAETD20203840&prefLang=en_US","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Orentas, Edvinas"]},{"key":"dc:creator","label":"Author","values":["Gegevičius, Rokas,"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2016"]},{"key":"dc:publisher","label":"Institution","values":["Institutional Repository of Vilnius University"]},{"key":"dc:relation","label":"Dc Relation","values":["https://epublications.vu.lt/object/elaba:20203840/20203840.pdf"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/bachelorThesis"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["lit"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://repository.vu.lt/VU:ELABAETD20203840&prefLang=en_US"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["To date, the Pictet−Spengler reaction of tryptophan derivatives remains a key strategic transformation for the stereospecific synthesis of macroline, sarpagine and ajmaline related indole alkaloids. As a consequence, the synthesis of congeners possessing oxygenated indole ring requires the optimization of enantioselective routes to the relevant oxygenated tryptophan analogues.By contrast, the potential of the 9-azabicyclo[3.3.1]nonane synthons for de novo construction of the indole moiety of cycloocta[b]indole core is considerably less explored. In this work, a generalized synthetic access to Sarpagine alkaloids through a new synthon based on 9-azabicyclo[3.3.1]nonane core is presented. Synthesis of a new precursor was accomplished in four steps enantioselectively and without protecting groups. Fischer indolization reaction to forge the natural product’s carbon framework was also investigated, which provided an access to Sarpagine related alkaloids and their synthetic analogues."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Optimalios sarpaginų šeimos alkaloidų sintezės paieška /","Towards an optimal synthesis of sarpagine alkaloids."]}]}],"canonical_facts":{"dc:contributor":["Orentas, Edvinas"],"dc:creator":["Gegevičius, Rokas,"],"dc:date":["2016"],"dc:description":["To date, the Pictet−Spengler reaction of tryptophan derivatives remains a key strategic transformation for the stereospecific synthesis of macroline, sarpagine and ajmaline related indole alkaloids. As a consequence, the synthesis of congeners possessing oxygenated indole ring requires the optimization of enantioselective routes to the relevant oxygenated tryptophan analogues.By contrast, the potential of the 9-azabicyclo[3.3.1]nonane synthons for de novo construction of the indole moiety of cycloocta[b]indole core is considerably less explored. In this work, a generalized synthetic access to Sarpagine alkaloids through a new synthon based on 9-azabicyclo[3.3.1]nonane core is presented. Synthesis of a new precursor was accomplished in four steps enantioselectively and without protecting groups. Fischer indolization reaction to forge the natural product’s carbon framework was also investigated, which provided an access to Sarpagine related alkaloids and their synthetic analogues."],"dc:format":["application/pdf"],"dc:identifier":["https://repository.vu.lt/VU:ELABAETD20203840&prefLang=en_US"],"dc:language":["lit"],"dc:publisher":["Institutional Repository of Vilnius University"],"dc:relation":["https://epublications.vu.lt/object/elaba:20203840/20203840.pdf"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:title":["Optimalios sarpaginų šeimos alkaloidų sintezės paieška /","Towards an optimal synthesis of sarpagine alkaloids."],"dc:type":["info:eu-repo/semantics/bachelorThesis"]},"updated_at":"2026-07-24T05:55:44Z"}