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.File in questo prodotto:
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