Organic Letters · 2015 · 48 citations · 18 references
Natural SciencesBiochemistryChemistryDrug DiscoveryOrganic ChemistryStructure-activity RelationshipsHeterocyclic ChemistryHeterocyclic CompoundsRetrosynthetic AnalysisTerpenoid BiosynthesisQuantum Chemical ModelingTriterpene BiosynthesisX-ray Diffraction Analysis
Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.
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