Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The 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.
Ključne reči:
Organocatalysis / Iminosugars / Fagomine / Pipecolic acids / Glycolipid storage disordersIzvor:
Tetrahedron, 2015, 71, 38, 6784-6789Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- Razvoj novih sintetičkih metoda i njihova primena u sintezi prirodnih proizvoda i biološki aktivnih jedinjenja (RS-MESTD-Basic Research (BR or ON)-172027)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
- humanitarian foundation Hrast
- Serbian Academy of Sciences and Arts [F193]
Napomena:
- This 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
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3390
DOI: 10.1016/j.tet.2015.07.036
ISSN: 0040-4020
WoS: 000359874300019
Scopus: 2-s2.0-84938976331
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marjanović-Trajković, Jasna AU - Ferjančić, Zorana AU - Saičić, Radomir PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3389 AB - The 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. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron T1 - Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids VL - 71 IS - 38 SP - 6784 EP - 6789 DO - 10.1016/j.tet.2015.07.036 ER -
@article{ author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir", year = "2015", abstract = "The 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.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron", title = "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids", volume = "71", number = "38", pages = "6784-6789", doi = "10.1016/j.tet.2015.07.036" }
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2015). Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron Pergamon-Elsevier Science Ltd, Oxford., 71(38), 6784-6789. https://doi.org/10.1016/j.tet.2015.07.036
Marjanović-Trajković J, Ferjančić Z, Saičić R. Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron. 2015;71(38):6784-6789. doi:10.1016/j.tet.2015.07.036 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids" in Tetrahedron, 71, no. 38 (2015):6784-6789, https://doi.org/10.1016/j.tet.2015.07.036 . .