A simple, modular synthesis of C4-substituted tryptophan derivatives
F Bartoccini1, S Bartolucci1, M Mari1
1Department of Biomolecular Sciences, University of Urbino "Carlo Bo", P.zza Rinascimento 6, 61029 Urbino, PU, Italy. giovanni.piersanti@uniurb.it.
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.
Related Concept Videos
Amino Acid Biosynthetic Pathways
Stereoisomerism of Cyclic Compounds
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

![Radiosynthesis of 1-2-[18F]Fluoroethyl-L-Tryptophan using a One-pot, Two-step Protocol](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F63025.jpg&w=3840&q=50)
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)