Asymmetric Total Synthesis of Euphordraculoate A and Pedrolide
Canhui Tu, Yunlong Yang, Yuzhi Jiang, Yan Hao, Zhen Wang, Shaomin Fu, Song Qin, Bo Liu
Abstract
Here we report the asymmetric total syntheses of two rearranged tigliane diterpenoids, euphordraculoate A and pedrolide. A reductive dihydroxylation cascade and Nazarov cyclization were performed to generate euphordraculoate A, which was subjected to a cascade of Eu-promoted dienyl enolization, intramolecular Diels-Alder reaction and enol-ketone tautomerization to afford pedrolide, a pathway consistent with our proposal for the biogenesis of pedrolide.
Topics & Concepts
TautomerIntramolecular forceEnolKetoneCascadeTotal synthesisDihydroxylationStereochemistryKeto–enol tautomerismChemistryHydroxylationBiogenesisEnantioselective synthesisOrganic chemistryCatalysisBiochemistryEnzymeChromatographyGeneSynthetic Organic Chemistry MethodsMicrobial Natural Products and BiosynthesisPlant-based Medicinal Research