The optimisation and stereoselective synthesis of a series of diketopiperazine oxytocin antagonists, leading to the discovery of Retosiban, will be described. The chemistry proceeds via an initial Ugi reaction using a versatile convertible isonitrile. Activation of the intermediate amido phenol followed by amine addition promotes epimerisation at the exocyclic position and yields the required diastereoisomer as the major product.

Optimization of a stereoselective Ugi reaction in the discovery of the oxytocin antagonist retosiban

243rd National Meeting (2012)

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