Construction of macrocyclic thiodepsipeptides: synthesis of a nosiheptide 'southern hemisphere' model system.
A 20-membered macrocyclic thiodepsipeptide has been synthesized as a model for the southern hemisphere of nosiheptide, the key steps being assembly of an acyclic precursor by amide coupling of indole and thiazole fragments followed by formation of the thiolactone in the macrocyclization step.
Kimber
Marc C
MC
School of Chemistry, University of Nottingham, University Park, Nottingham, UK.
Moody
Christopher J
CJ
D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D008968:Molecular Conformation; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
D047630:Depsipeptides; D047028:Macrocyclic Compounds; D013438:Sulfhydryl Compounds; D013844:Thiazoles; C014134:nosiheptide