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Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids

dc.creatorMarjanović-Trajković, Jasna
dc.creatorFerjančić, Zorana
dc.creatorSaičić, Radomir
dc.date.accessioned2019-09-09T12:01:21Z
dc.date.available2019-09-09T12:01:21Z
dc.date.issued2015
dc.identifier.issn0040-4020
dc.identifier.urihttps://cherry.chem.bg.ac.rs/handle/123456789/3389
dc.description.abstractThe enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized.en
dc.publisherPergamon-Elsevier Science Ltd, Oxford
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS//
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/256716/EU//
dc.relationhumanitarian foundation Hrast
dc.relationSerbian Academy of Sciences and Arts [F193]
dc.rightsembargoedAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceTetrahedron
dc.subjectOrganocatalysisen
dc.subjectIminosugarsen
dc.subjectFagomineen
dc.subjectPipecolic acidsen
dc.subjectGlycolipid storage disordersen
dc.titleOrganocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acidsen
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractМарјановић-Трајковић, Јасна; Ферјанчић, Зорана; Саичић, Радомир;
dc.citation.volume71
dc.citation.issue38
dc.citation.spage6784
dc.citation.epage6789
dc.identifier.wos000359874300019
dc.identifier.doi10.1016/j.tet.2015.07.036
dc.citation.rankM22
dc.description.otherThis is the peer-reviewed version of the following article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. [https://doi.org/10.1016/j.tet.2015.07.036]
dc.description.otherSupplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3390]
dc.type.versionacceptedVersionen
dc.identifier.scopus2-s2.0-84938976331
dc.identifier.fulltexthttps://cherry.chem.bg.ac.rs/bitstream/id/14783/Organocatalyzed_synthesis_of_acc_2015.pdf


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