Synthetic Communications p. 2350 - 2356 (2019)
Update date:2022-08-03
Topics:
Sasane, Sachin A.
Bhise, Nandu B.
Singh, Girij P.
Joseph, Alex
Shenoy, Gautham G.
An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20 = +35.37° (c = 0.90, 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.
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