- A β-lactam-based stereoselective access to β,γ-dihydroxy α-amino acid-derived peptides with either α,β-like or unlike configurations
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A concise access to α,β-dihydroxy α-amino acid-derived N-carboxy anhydrides (NCAs) with either like or unlike relative configuration is described. The key steps of the synthetic route are the preparation of the nonracemic 4-alkenyl β-lactams, through either Homer-type olefination of a common 4-formyl β-lactam or the Corey-Winter alkene synthesis applied to 4-dihydroxyalkyl β-lactams, followed by the Sharpless AD reaction, and a subsequent ring expansion of the corresponding 4-substituted 3-hydroxy β-lactams promoted by TEMPO. The opening of thus-prepared NCAs upon treatment with different O- and N-nucleophiles, including α-amino esters which lead to peptides, has also been studied under various reaction conditions.
- Palomo,Oiarbide,Landa,Esnal,Linden
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p. 4180 - 4186
(2007/10/03)
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- A strategy for the asymmetric aminohomologation of α,β-dihydroxy aldehydes: Application to the synthesis of the southwest tripeptide segment of echinocandin B
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The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic
- Palomo, Claudio,Oiarbide, Mikel,Landa, Aitor
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