Tandem deprotection-dimerization-macrocyclization route to C(2) symmetric cyclo-tetrapeptides.
Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo-dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200 (USA).
Khanh
K
Ha
Iryna
I
Lebedyeva
Sadra
S
Hamedzadeh
Zhiliang
Z
Li
Ryan
R
Quiñones
Girinath G
GG
Pillai
Byron
B
Williams
Amir
A
Nasajpour
Kristin
K
Martin
Abdullah M
AM
Asiri
Alan R
AR
Katritzky
D003500:Cyclization; D019281:Dimerization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D047028:Macrocyclic Compounds; D010456:Peptides, Cyclic; D014230:Triazoles; D010165:Palladium; C012771:benzotriazole
benzotriazoles; cyclodimerization; lactamization; macrocycles; peptides