2985-33-3Relevant articles and documents
Aspidosperma Alkaloids via Cyclization of Secodine Intermediate: Synthesis of (+/-)-3-Oxovincadifformine Ethyl Ester
Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni,Passarella, Daniele,Silvani, Alessandra
, p. 6941 - 6954 (1994)
(+/-)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular cycloaddition of the 3-oxosecodine 13 first prepared in turn from the enamide 10 by dehydrogenation with benzeneseleninic anhydride.An insight into the conversion of 10 into 13 was gained, resulting in the suggestion of a plausible mechanistic pathway.
Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides
Porey, Arka,Mondal, Bhaskar Deb,Guin, Joyram
supporting information, p. 8786 - 8791 (2021/03/17)
Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.
4-Hydroxy-3-methyl-2(1h)-quinolone, originally discovered from a brassicaceae plant, produced by a soil bacterium of the genus burkholderia sp.: Determination of a preferred tautomer and antioxidant activity
Igarashi, Yasuhiro,Kurokawa, Yoichi,Li, Dandan,Oku, Naoya,Shinozaki, Yukiko
supporting information, p. 1489 - 1494 (2020/07/08)
4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria without providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related compounds and a synthetic preparation of 1, allowed its first full NMR characterization and identification of 2-quinolone but not 2-quinolinol (2) as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, compound 1 at 10 μM, a concentration lower than that in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86percent. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response in the host organisms.
