Synthesis of (2S, 3R, 4S), (2S, 3S, 4R)-epoxyprolines and aminohydroxyprolines
Preparations of epoxy and aminohydroxyprolines from trans-4-hydroxy-L-proline are described.
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Stereocontrolled synthesis of glycosidase inhibitors (+)-hyacinthacines A<inf>1</inf> and A<inf>2</inf>
2015, Tetrahedron AsymmetryChapter 8 Correlations through space. The nuclear Overhauser effect
2009, Tetrahedron Organic Chemistry SeriesCitation Excerpt :In these cases, it is wise to collect as many NOE enhancements as is possible for the sample and to ensure self-consistency over all of these within the proposed stereochemistry. These points are exemplified by the configurational assignment of the synthesised epoxyprolines [5] 8.4a and 8.4b. The negligible J-coupling between H2 and H3 in 8.4a tentatively suggested these protons to be trans, and the slightly greater 2.5 Hz coupling in 8.4b suggested these share a cis relationship.
One-pot synthesis of azanucleosides from proline derivatives
2008, Tetrahedron LettersFirst total synthesis of penmacric acid and its stereoisomer
2007, Tetrahedron LettersSelenocyclisations of homoallylic sulfonamides: stereoselective methods for the elaboration of substituted pyrrolidines, pyrrolines and derivatives
2006, TetrahedronCitation Excerpt :In view of the foregoing results, we also chose to restrict this investigation to the seemingly more awkward aryl substituted alkenes. Hence, the cinnamyl glycinate 51 was chosen as the first test substrate; this was readily prepared from cinnamyl bromide and the enolate of N-benzylidene glycinate using the excellent Stork procedure,27 followed by exchange of the protecting group.19 When subjected to ‘thermodynamic’ conditions (Scheme 4), once again mixtures of the 2,5-cis and trans selanyl-pyrrolidines were obtained.