Direct, regioselective, and chemoselective preparation of novel boronated tryptophans by Friedel-Crafts alkylation.
A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.
Department of Biomolecular Sciences, University of Urbino, Piazza Rinascimento 6, 61029 Urbino (PU), Italy.
Silvia
S
Bartolucci
Francesca
F
Bartoccini
Marika
M
Righi
Giovanni
G
Piersanti
D000478:Alkylation; D017605:Bromine Compounds / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D017605:Bromine Compounds; D014364:Tryptophan