Total synthesis of sulfobacin A through dynamic kinetic resolution of a racemic β-keto-α-amino ester hydrochloride

Add time:09/10/2019    Source:sciencedirect.com

A total synthesis of sulfobacin A, a von Willebrand factor receptor antagonist, is described. Our synthetic approach relies uniquely on catalytic asymmetric reactions for the creation of the three stereogenic centers without using chiral building blocks. The key steps of this short route to sulfobacin A involve ruthenium-mediated asymmetric hydrogenation reactions of a β-keto ester and a racemic β-keto-α-amino ester hydrochloride to afford, respectively, the corresponding enantiomerically pure β-hydroxy ester and the enantioenriched anti β-hydroxy α-amino ester hydrochloride through dynamic kinetic resolution.

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