Synthetic Communications | 2019
An improved synthesis of latanoprost involving effective control on 15(S) diastereomer
Abstract
Abstract An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20\u2009=\u2009+35.37° (c\u2009=\u20090.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection. GRAPHICAL ABSTRACT