Direct synthesis of the antitumor agent -α-amino-3-bromo-4,5-dihydroisoxazole-5-acetic acid

Synthesis and in vitro/in vivo Evaluation of the Antitrypanosomal Activity of 3‐Bromoacivicin, a Potent CTP Synthetase Inhibitor

“…The synthesis of 3-bromoacivicin in a racemic form was previously described. 7 However, a survey of the literature shows that an efficient preparation of enantiomerically pure (α S ,5 S )-3-bromoacivicin has never been described; the only reported methods require multistep procedures and rely on resolution of racemic mixtures through the formation of diastereomeric salts followed by crystallization. 8…”

Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio‐and Diastereoselectivities

“…4-Cyclopentene-1,3-dione (9), was purchased from Aldrich and always sublimed before use. The reaction was then treated with a saturated solution of NH 4 Cl and extracted with diethyl ether (at least three times). The ethereal extracts were dried on anhydrous Na 2 SO 4 and the solvent was evaporated under reduced pressure.…”

“…The aqueous solution was treated with solid KOH to pH ϭ 10, saturated with NaCl and extracted with diethyl ether. The ethereal extracts were dried on anhydrous Na 2 SO 4 …”

“…When the starting compound disappeared (TLC; petroleum ether/diethyl ether, 1:3), the solution was diluted with water (20 mL) and extracted with dichloromethane. The organic extracts were dried with Na 2 SO 4 …”

Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

“…Isoxazolines are valuable intermediates for obtaining β-hydroxy ketones or γ-amino alcohols 1 but they are also important in their being possibly endowed with biological activity or lending themselves to further transformations leading to natural products or pharmacologically active compounds. [2][3][4][5][6][7][8] The 1,3-dipolar cycloaddition of nitrile oxides to alkenes has been one of the most general methods used for the preparation of isoxazoline derivatives. 9- 12 This reaction is both regio-and stereo-selective and the selectivity is enhanced in alkenes bearing an allylic chiral centre.…”