Propellane as a conformational device for the stabilization of the β-lactone of salinosporamide A

The synthesis of a propellane derivative of salinosporamide A having increased stability under physiological-like conditions is reported. The synthesis took advantage of a substrate-controlled stereoselective Ugi 4-center 3-component reaction to construct the required syn-bicyclic pyroglutamic acid framework.

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