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The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost |
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| Authors: | Giuseppe Zanoni,Alessandro D&rsquo Alfonso,Lazzaro Feliciani,Giovanni Vidari |
| Affiliation: | a Department of Organic Chemistry, University of Pavia, Viale Taramelli, 10-27100 Pavia, Italy b Sifavitor S.r.l. Mairano di Casaletto Lodigiano, 26852 Lodi, Italy c EaStCHEM School of Chemistry, University of St. Andrews, KY16 9ST, United Kingdom |
| 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. |
| Keywords: | Anti-glaucoma drug Meyer-Schuster rearrangement Gold Chemistry Prostanoids syntheses Total synthesis |
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