An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

Joseph, Alex and Shenoy, Gautham G (2019) An improved synthesis of latanoprost involving effective control on 15(S) diastereomer. Synthetic Communications, 49 (18). pp. 1-8. ISSN 1532-2432

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Abstract

An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [a]D 20¼þ35.37� (c¼0.90, 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

Item Type: Article
Uncontrolled Keywords: Crystallization; diol intermediate; ketone intermediate; latanoprost; p-nitrobenzoyl chloride; preparative HPLC
Subjects: Pharmacy > MCOPS Manipal > Pharmaceutical Chemistry
Depositing User: KMC Library
Date Deposited: 17 Aug 2019 05:52
Last Modified: 17 Aug 2019 05:52
URI: http://eprints.manipal.edu/id/eprint/154379

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