128891-66-7Relevant articles and documents
Asymmetric Total Synthesis and Biological Evaluation of Proapoptotic Natural Myrcene-Derived Cyclohexenyl Chalcones
Tiamas, Shelly Gapil,Audet, Florian,Samra, Alma Abou,Bignon, Jérome,Litaudon, Marc,Fourneau, Christophe,Ariffin, Azhar,Awang, Khalijah,Desrat, Sandy,Roussi, Fanny
, p. 5830 - 5835 (2018)
Based on a bioinspired asymmetric Diels–Alder cycloaddition using a chiral Evans oxazolidinone, the first total synthesis of both enantiomers of two myrcene-derived cyclohexenyl chalcones, fislatifolione and fislatifolic acid, has been carried out. This strategy was also applied to the total synthesis of nicolaiodesin C. These natural products, as well as their synthetic intermediates, were evaluated by in-vitro affinity displacement assays, based on the modulation of Bcl-xL/Bak, Mcl-1/Bid, and Bcl-2-Bim interactions. This study showed that (+)-fislatifolic acid acts as a dual Bcl-xL/Mcl-1 inhibitor with micromolar activity, and that a Weinreb amide intermediate acts as an excellent Mcl-1/Bcl-2 dual inhibitor at the submicromolar level.
Palladium-catalyzed diastereoselective synthesis of β,β-diarylpropionic acid derivatives and its application to the total synthesis of (R)-tolterodine and the enantiomer of a key intermediate for MK-8718
Zhi, Wubin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 537 - 540 (2018/01/17)
Palladium-catalyzed diastereoselective synthesis of optically active β,β-diarylpropionic acid derivatives employing 4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary under an air atmosphere in excellent yields with high diastereoselectivity is reported. The catalytic system is applied to the total synthesis of (R)-tolterodine and the enantiomer of a key intermediate for MK-8718.
Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: Synthesis of chiral fluorinated amino acids
Erdbrink, Holger,Peuser, Ilona,Gerling, Ulla I. M.,Lentz, Dieter,Koksch, Beate,Czekelius, Constantin
supporting information, p. 8583 - 8586 (2013/01/15)
A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.
