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Gold(I) mediated MeyereSchuster rearrangement for the installation of the ‘lower’ side chain of pros- taglandins 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 ef␣cient alternative to the standard HornereWadswortheEmmons 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.

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

ZANONI, GIUSEPPE;PORTA, ALESSIO;VIDARI, GIOVANNI
2010-01-01

Abstract

Gold(I) mediated MeyereSchuster rearrangement for the installation of the ‘lower’ side chain of pros- taglandins 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 ef␣cient alternative to the standard HornereWadswortheEmmons 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.
2010
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
TETRAHEDRON
sì
WOS:000281836300003
2-s2.0-77956178314
Esperti anonimi
Inglese
Internazionale
STAMPA
66
7472
7478
7
Gold Chemistry; Prostaglandin; Bimatoprost; Latanoprost.
sì
6
info:eu-repo/semantics/article
262
Zanoni, Giuseppe; D’Alfonso, Alessandro; Porta, Alessio; Feliciani, Lazzaro; Nolan, Steve; Vidari, Giovanni
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/356527
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