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

Sachin A. Sasane, Nandu B. Bhise, Girij P. Singh, Alex Joseph, Gautham G. Shenoy

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)2350-2356
Number of pages7
JournalSynthetic Communications
Volume49
Issue number18
DOIs
Publication statusPublished - 17-09-2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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