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An Asymmetric Suzuki–Miyaura Approach to Prostaglandins: Synthesis of Tafluprost

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journal contribution
posted on 27.03.2020, 12:06 by Roman Kučera, F. Wieland Goetzke, Stephen P. Fletcher
We report the catalytic asymmetric synthesis of Tafluprost (1), 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.