The highly chemo- and enantioselective hydrogenation of (E)-2-substituted-4-oxo-2-alkenoic acids was established for the first time using the Rh/JosiPhos complex, affording a series of chiral α-substituted-γ-keto acids with excellent results (up to 99% yield and >99% ee) and high efficiency (up to 3000 TON). In addition, the importance of this methodology was further demonstrated by a concise and gram-scale synthesis of the anti-inflammatory drug (R)-flobufen.

19 Sep 2018·Journal of the American Chemical SocietyQ1 · CHEMISTRY

Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

Q1 · CHEMISTRY

Article

Author: Zhou, Qi-Lin ; Li, Ming-Ming ; Xie, Jian-Hua ; Cheng, Lei ; Xiao, Li-Jun

We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of ( R)-flobufen.

01 Apr 2008·TalantaQ2 · CHEMISTRY

Liquid chromatographic–electrospray mass spectrometric determination (LC–ESI-MS) of phase II metabolites of flobufen in rat liver microsomes—Chiral discrimination

Q2 · CHEMISTRY

Article

Author: Petr Solich ; Vladimír Wsól ; Michal Němec ; Yogeeta N. Babú

Glucuronidation of the non-steroidal anti-inflammatory chiral drug flobufen and its major metabolite M17203 has been implicated as an important mechanism of flobufen elimination. To characterize flobufen metabolism by O-glucuronidation, new liquid chromatographic method (LC) coupled with ESI-MS was developed to detect the conjugates of flobufen and its metabolites formed in vitro in rat liver microsomes. Discovery DSC-18 LT cartridge columns were utilized for solid phase extraction (SPE) and Discovery C18 column (150 mm x 2.1 mm, 5 microm particle size) was used for LC separation. Chiral inversion of flobufen and its metabolites enantiomers was checked by special 1-allyl-(5R,8S,10R)-terguride column (150 mm x 4.6 mm). O-Glucuronidation of the S-enantiomer displayed a typical Michaelis-Menten kinetics, whereas the R-enantiomer exhibited a substrate inhibition type of kinetics. The study of glucuronidation of M17203 led to kinetics with sigmoidal characteristics.

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Indication	Highest Phase	Country/Location	Organization	Date
Rheumatic Diseases	Phase 3	-	Vufb A S	-
Rheumatic Diseases	Phase 3	CZ	-	-

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