title: A simple, modular synthesis of C4-substituted tryptophan derivatives.
abstract: The modular and versatile synthesis of C4-substituted tryptophan derivatives by direct functionalization of easily available N-acetyl 4-boronate tryptophan methyl ester via transition metal-catalyzed and metal-mediated cross coupling reactions is described. The versatility of the chemistry is highlighted by the gram-scale synthesis of 4-boronated N-acetyl-tryptophan methyl ester and the rapid synthesis of C4-aryl, C4-alkyl, C4-cyano, C4-trifluoromethyl, C4-azido, and C4-hydroxy tryptophan derivatives. The utility of our methodology is illustrated through the quick approach to the tricyclic azepino indole skeleton embedded in many natural products.
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, PU, Italy. giovanni.piersanti@uniurb.it.
authors.forename: F
authors.initials: F
authors.lastname: Bartoccini
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, PU, Italy. giovanni.piersanti@uniurb.it.
authors.forename: S
authors.initials: S
authors.lastname: Bartolucci
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, PU, Italy. giovanni.piersanti@uniurb.it.
authors.forename: M
authors.initials: M
authors.lastname: Mari
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, PU, Italy. giovanni.piersanti@uniurb.it.
authors.forename: G
authors.initials: G
authors.lastname: Piersanti
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000737:chemistry; D014364:Tryptophan / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007211:Indoles; D014364:Tryptophan