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Asymmetric Synthesis of a Pyrrolizidinone‐Based hNK1 Antagonist through Reductive Ring Contraction of a Six‐Membered Cyclic Nitronate

Von Wiley-VCH zur Verfügung gestellt

A concise 7-step asymmetric synthesis of MSD’s potent hNK 1 antagonist containing a pyrrolizidinone core bearing two fluorine-substituted aryl groups was developed. The pyrrolizidinone unit was constructed by reductive recyclization of a properly functionalized cyclic nitronate, which was assembled by stereoselective [4+2]-cycloaddition of a nitroalkene with a vinyl ether bearing a Whitesell’s chiral auxiliary group. The configuration of the hNK 1 antagonist, which was previously suggested based on bioactivity data, was confirmed by X-ray analysis. The crystal structure features multiple weak interactions involving fluorine atoms that are also found in a complex with the hNK 1 receptor simulated by molecular docking.

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