Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone.

Journal article

(4R,5R)-Cytoxazone has been prepared in four steps and in 61% overall yield and >98% ee. Conjugate addition of lithium (R)-N-benzyl-N-[small alpha]-methylbenzylamide to tert-butyl (E)-3-(p-methoxyphenyl)prop-2-enoate and subsequent in situ diastereoselective enolate oxidation with (+)-(camphorsulfonyl)oxaziridine gave tert-butyl (2R,3R,[small alpha]R)-2-hydroxy-3-(p-methoxyphenyl)-3-(N-benzyl-N-[small alpha]-methylbenzylamino)propanoate in >98% de. Subsequent N-benzyl deprotection to th...

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Authors: Davies, S; Hughes, D; Nicholson, R; Smith, A; Wright, A

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 2
• Issue: 10
• Pages: 1549-1553
• Publication date: 2004-05-01
• DOI: 10.1039/b402437k
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Magnetic Resonance Spectroscopy; Molecular Conformation; Oxazoles; Oxidation-Reduction; Stereoisomerism; Oxazolidinones; Heterocyclic Compounds, 2-Ring; Molecular Structure; Cyclization