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.
Titolo: | Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-delta-hydroxyisoleucine, noncoded amino acid of halipeptin A | |
Autori: | ||
Data di pubblicazione: | 2004 | |
Rivista: | ||
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 |
File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.