Synthesis · 2013 · 12 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisMacrocycle DiversificationMacrocycle Library SynthesisMacrocyclic Library SynthesisRegioselective HydrolysisRing-forming ReactionsThiadiazole ChemistryThiazole ChemistryThiazole Synthesis
The synthesis of a 28-membered thiopeptide macrocycle is described. Key steps are mild aza-Wittig thiazole ring closures, a scandium(III)-mediated regioselective ester hydrolysis, and a highly efficient macrolactam formation with its 3-hydroxypyridine nucleus orthogonally protected.