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

doi:10.1080/00397911.2019.1622018

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 journal › Article › peer-review

3 Citations (Scopus)

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 language	English
Pages (from-to)	2350-2356
Number of pages	7
Journal	Synthetic Communications
Volume	49
Issue number	18
DOIs	https://doi.org/10.1080/00397911.2019.1622018
Publication status	Published - 17-09-2019

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1080/00397911.2019.1622018

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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.",

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AU - Sasane, Sachin A.

AU - Bhise, Nandu B.

AU - Singh, Girij P.

AU - Joseph, Alex

AU - Shenoy, Gautham G.

PY - 2019/9/17

Y1 - 2019/9/17

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AB - 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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JO - Synthetic Communications

JF - Synthetic Communications

IS - 18

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

Abstract

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