Stereoselective formal synthesis of the potent proteasome inhibitor: salinosporamide A

Stereoselective formal synthesis of the potent proteasome inhibitor: salinosporamide A

(2 R,3 S)-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 a...

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Veröffentlicht in:Tetrahedron letters 2007-01, Vol.48 (3), p.381-384
Hauptverfasser: Caubert, Virginie, Massé, Julien, Retailleau, Pascal, Langlois, Nicole
Format: Artikel
Sprache:eng
Schlagworte:
1,3-Dipolar cycloadditions
Chemical Sciences
N-Methylnitrone
Organic chemistry
Proteasome inhibitor
Pyroglutamate
Salinosporamide A
Selective O-benzylation
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Zusammenfassung:(2 R,3 S)-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.11.087