Synthesis of SK&F 104353

Significance

Good yields, high trans-selectivity and high enantioselectivities are the hallmarks of a synthesis of glycidic amides that have been applied to the synthesis of SK&F 104353, a leuko-triene D₄ inhibitor with potential for the treatment of bronchial asthma. A previous synthesis achieved asymmetric epoxidation using a Julia-Colonna epoxidation of an α,β-unsaturated ketone with a polyleucine catalyst; see: I. Lantos et al. J. Org. Chem. 1993, 58, 6247-6254.