A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diels-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)- oxazolones and β-sulfanyl-α-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the α,α-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized.

Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues / A. Ruffoni, A. Casoni, S. Pellegrino, M.L. Gelmi, R. Soave, F. Clerici. - In: TETRAHEDRON. - ISSN 0040-4020. - 68:7(2012), pp. 1951-1962.

Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues

A. Ruffoni
Primo
;
A. Casoni
Secondo
;
S. Pellegrino;M.L. Gelmi;R. Soave
Penultimo
;
F. Clerici
Ultimo
2012

Abstract

A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diels-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)- oxazolones and β-sulfanyl-α-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the α,α-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/174450
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