The Journal of Organic Chemistry · 2012 · 14 citations · 31 references
PharmacyChemistryMedicinal ChemistryDrug DesignStructure-activity RelationshipsSynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisRetrosynthetic AnalysisAbsolute Configuration AssignmentAbsolute Configuration DeterminationMacrocyclic Library SynthesisRing-closing MetathesisRing-forming ReactionsTotal Synthesis-derived Analogues
The total synthesis of the putative structure of stagonolide D has been completed. The relative and absolute configuration of stagonolide D was established by synthesizing its optical antipode. The adopted strategy involves the construction of the central macrolide employing ring-closing metathesis (RCM), followed by selective protecting group manipulations and a final concomitant -OTBS deprotection and displacement of an -OMs placed next to it, resulting in the formation of the epoxide ring.
31