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

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latanoprost
Hydroxyl Radical
Crystallization
Purification

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Sasane, Sachin A. ; Bhise, Nandu B. ; Singh, Girij P. ; Joseph, Alex ; Shenoy, Gautham G. / An improved synthesis of latanoprost involving effective control on 15(S) diastereomer. In: Synthetic Communications. 2019 ; Vol. 49, No. 18. pp. 2350-2356.
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An improved synthesis of latanoprost involving effective control on 15(S) diastereomer. / Sasane, Sachin A.; Bhise, Nandu B.; Singh, Girij P.; Joseph, Alex; Shenoy, Gautham G.

In: Synthetic Communications, Vol. 49, No. 18, 17.09.2019, p. 2350-2356.

Research output: Contribution to journalArticle

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