A novel general route for the synthesis of C-glycosyl tyrosine analogues.
A general method for the synthesis of C-glycosyl amino acids is described here. The stereoisomerically pure tyrosine analogues alpha-L-4 and beta-L-6 are prepared in reasonable overall yields from allyl derivatives 10 and 11. The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.
Brenna
Elisabetta
E
Dipartmento di Chimica del Politecnico, Centro CNR per lo Studio del Sostanze Organiche Naturali, Milano, Italy. brenna@dept.chem.polimi.it
Fuganti
Claudio
C
Grasselli
Piero
P
Serra
Stefano
S
Zamboti
Sabrina
S
D003640:Dealkylation; D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D006027:Glycosides; D007202:Indicators and Reagents; D014443:Tyrosine