title: Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate.
abstract: Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol, BS8 1TS, U.K.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Prévost
authors.forename: Karen
authors.initials: K
authors.lastname: Thai
authors.forename: Nina
authors.initials: N
authors.lastname: Schützenmeister
authors.forename: Graeme
authors.initials: G
authors.lastname: Coulthard
authors.forename: William
authors.initials: W
authors.lastname: Erb
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000069580:Bimatoprost; D003008:Cloprostenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015237:Dinoprost / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000077338:Latanoprost; D015394:Molecular Structure; D011461:Prostaglandins F, Synthetic / Q000138:chemical synthesis* / Q000737:chemistry; D011465:Prostaglandins, Synthetic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000577:Amides; D011461:Prostaglandins F, Synthetic; D011465:Prostaglandins, Synthetic; D003008:Cloprostenol; D000077338:Latanoprost; C116609:3-hydroxybutanal; D015237:Dinoprost; D000069580:Bimatoprost