Tris(pentafluorophenyl)borane has found to be an effective catalyst for the alkylation of 1,3-dicarbonyl compounds using benzylic alcohols as alkylating agents. Various 1,3-dicarbonyl compounds reacted cleanly with different benzylic alcohols to provide the corresponding monoalkylated products in good yield. In addition tris(pentafluorophenyl)borane efficiently promoted the C3 alkylation of 4-hydroxycoumarins. Further, several oxygenated heterocycles such as furans, 4H-chromenes, and furanocoumarins have been prepared using the described methodology as the key step.

An efficient approach has been described for the synthesis of 3,5‐disubstituted isoxazoles from propargylic alcohols. The strategy involves a one‐pot p‐TSA‐catalyzed N‐propargylation of protected hydroxylamines followed by a TBAF‐mediated detosylative 5‐endo‐dig cyclization. The method was successfully used for the synthesis of various 3,5‐disubstituted isoxazoles.

17­(R),18­(S)-Epoxyeicosatetraenoic acid (EEQ) is a cytochrome P450 metabolite of eicosapentaenoic acid (EPA) and a powerful negative chronotrope with low nanomolar activity in a neonatal rat cardiomyocyte (NRCM) arrhythmia model. Prior studies identified oxamide 2b as a soluble epoxide hydrolase (sEH) stable replacement but unsuitable for in vivo applications due to limited oral bioavailability and metabolic stability. These ADME limitations have been addressed in an improved generation of negative chronotropes, e.g., 4 and 16, which were evaluated as potential clinical candidates.

International audienc

One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Propargylic Alcohols Through Propargylic N-Hydroxylamines. -A mild and efficient synthesis of propargylic N-hydroxylamines from propargylic alcohols is described and successfully extended to a one-pot synthesis of 3,5-disubstituted isoxazoles. -(REDDY*, C. R.; VIJAYKUMAR, J.; JITHENDER, E.; REDDY, G. P. K.; GREE, R.; Eur. J. Org. Chem. 2012, 29, 5767-5773, http://dx.doi.org/10.1002/ejoc.201200628 ; Div. Nat. Prod. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -Bartels 15-124