An Asymmetric Suzuki–Miyaura Approach to Prostaglandins: Synthesis of Tafluprost
Roman Kučera, F. Wieland Goetzke, Stephen P. Fletcher
Abstract
), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki-Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji-Trost reaction with an enolate surrogate.
Topics & Concepts
ChemistryDesymmetrizationEnantioselective synthesisCatalysisStereochemistryAsymmetric hydrogenationBoronic acidBicyclic moleculeTrifluoromethanesulfonateCombinatorial chemistryOrganic chemistryAsymmetric Synthesis and CatalysisFluorine in Organic ChemistryCyclopropane Reaction Mechanisms