Assembling heterocycle-tethered C-glycosyl and alpha-amino acid residues via 1,3-dipolar cycloaddition reactions.
The 1,3-dipolar cycloadditions of C-glycosyl nitrile oxides and acetylenes to an alkyne and an azide, respectively, bearing a masked glycinyl moiety furnished disubstituted isoxazoles and triazoles. Unveiling the glycinyl group in these cycloadducts afforded C-glycosyl alpha-amino acids in which the two bioactive entities were tethered through rigid five-membered heterocycles. Optimized entries to the same compounds involved the use of unmasked but protected alkyne- and azide-containing amino acids as the partners of 1,3-dipolar cycloadditions.
Laboratorio di Chimica Organica, Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy. adn@dns.unife.it
Alessandro
A
Dondoni
Pier Paolo
PP
Giovannini
Alessandro
A
Massi
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D001386:Azides; D006027:Glycosides; D000409:Alanine; D005998:Glycine