TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=77956178314&partnerID=8YFLogxK
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 -