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EnglishThe first enantioselective synthesis of N,O-diprotected (2S,3S)-N-methyl-delta-hydroxyisoleucine 4, starting from readily available (tert-butyldimethylsilyl)-2-butyn-1-ol 5, is described. The key steps of this stereochemical flexible synthetic route involve a silyl-assisted [3,3]-sigmatropic rearrangement, for the establishment of the correct stereoisomeric pattern, and a triethylsilane–TFA induced reduction of an oxazolidinone intermediate, to yield the requested N-methylation.
http://hdl.handle.net/11386/1059575| Titolo: | Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-delta-hydroxyisoleucine, noncoded amino acid of halipeptin A |
| Autori interni: | IZZO, Irene MAULUCCI, Nakia DE RICCARDIS, Francesco |
| Data di pubblicazione: | 2004 |
| Rivista: | TETRAHEDRON-ASYMMETRY |
| Abstract: | The first enantioselective synthesis of N,O-diprotected (2S,3S)-N-methyl-delta-hydroxyisoleucine 4, starting from readily available (tert-butyldimethylsilyl)-2-butyn-1-ol 5, is described. The key steps of this stereochemical flexible synthetic route involve a silyl-assisted [3,3]-sigmatropic rearrangement, for the establishment of the correct stereoisomeric pattern, and a triethylsilane–TFA induced reduction of an oxazolidinone intermediate, to yield the requested N-methylation. |
| Handle: | http://hdl.handle.net/11386/1059575 |
| Appare nelle tipologie: | 1.1.2 Articolo su rivista con ISSN |
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