The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

Giuseppe Zanoni; Alessandro D'Alfonso; Alessio Porta; Lazzaro Feliciani; Steven Patrick Nolan; Giovanni Vidari

doi:10.1016/j.tet.2010.07.069

The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

Giuseppe Zanoni, Alessandro D'Alfonso, Alessio Porta, Lazzaro Feliciani, Steven Patrick Nolan, Giovanni Vidari

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

Abstract

Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7472-7478
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2010.07.069
Publication status	Published - 18 Sept 2010

Keywords

Anti-glaucoma drug
Meyer-Schuster rearrangement
Gold Chemistry
Prostanoids syntheses
Total synthesis
GOLD
KETONES
CATALYSIS

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title = "The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost",

abstract = "Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Anti-glaucoma drug, Meyer-Schuster rearrangement, Gold Chemistry, Prostanoids syntheses, Total synthesis, GOLD, KETONES, CATALYSIS",

author = "Giuseppe Zanoni and Alessandro D'Alfonso and Alessio Porta and Lazzaro Feliciani and Nolan, \{Steven Patrick\} and Giovanni Vidari",

year = "2010",

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T1 - The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

AU - Zanoni, Giuseppe

AU - D'Alfonso, Alessandro

AU - Porta, Alessio

AU - Feliciani, Lazzaro

AU - Nolan, Steven Patrick

AU - Vidari, Giovanni

PY - 2010/9/18

Y1 - 2010/9/18

N2 - Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

AB - Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Anti-glaucoma drug

KW - Meyer-Schuster rearrangement

KW - Gold Chemistry

KW - Prostanoids syntheses

KW - Total synthesis

KW - GOLD

KW - KETONES

KW - CATALYSIS

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U2 - 10.1016/j.tet.2010.07.069

DO - 10.1016/j.tet.2010.07.069

M3 - Article

SN - 0040-4020

VL - 66

SP - 7472

EP - 7478

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

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Keywords

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