Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization.
[structure: see text] An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.
Hernández
Delia
D
Barcelona Science Park Josep Samitier 1-5, E-08028 Barcelona, Spain.
Vilar
Gemma
G
Riego
Estela
E
Cañedo
Librada M
LM
Cuevas
Carmen
C
Albericio
Fernando
F
Alvarez
Mercedes
M
D003500:Cyclization; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
C519121:IB-01211; D010080:Oxazoles; D010456:Peptides, Cyclic