Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Sébastien Prévost; Karen Thai; Nina Schützenmeister; Graeme Coulthard; William Erb; Varinder K. Aggarwal

doi:10.1021/ol503520f

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Sébastien Prévost
, Karen Thai
, Nina Schützenmeister
, Graeme Coulthard
, William Erb
, Varinder K. Aggarwal

University of Bristol

Research output: Contribution to journal › Article › peer-review

47 Citations (Scopus)

Abstract

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF_2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

Original language	English
Pages (from-to)	504-507
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503520f
Publication status	Published - 6 Feb 2015
Externally published	Yes

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title = "Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate",

abstract = "Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99\% ee.",

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AU - Prévost, Sébastien

AU - Thai, Karen

AU - Schützenmeister, Nina

AU - Coulthard, Graeme

AU - Erb, William

AU - Aggarwal, Varinder K.

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

AB - Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

U2 - 10.1021/ol503520f

DO - 10.1021/ol503520f

M3 - Article

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AN - SCOPUS:84922594721

SN - 1523-7060

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EP - 507

JO - Organic Letters

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ER -

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

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