Stereoselective formal synthesis of the potent proteasome inhibitor: salinosporamide A |
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| Authors: | Virginie Caubert |
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| Affiliation: | Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France |
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| Abstract: | (2R,3S)-α-Methylenelactam 3, the key intermediate in Corey’s syntheses of salinosporamide A, has been synthesized from (S)-methyl 2-hydroxymethylpyroglutamate through chemoselective O-protection, regio- and stereoselective N-methylnitrone cycloaddition and quaternarization-elimination reactions as the main steps. |
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| Keywords: | Proteasome inhibitor Salinosporamide A Pyroglutamate 1,3-Dipolar cycloadditions N-Methylnitrone Selective O-benzylation |
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