Total Synthesis of (±)-Rubriflordilactone A
Xudong Zheng, Xinlong Guo, Hongyu Wang, Panpan Zhou, Xiaoming Chen
Abstract
A new and efficient synthesis of rubriflordilactone A has been realized. The key transformations include the following: (1) an intramolecular Prins cyclization to establish the seven-membered ring containing two contiguous stereocenters; (2) a Mukaiyama hydration/oxa-Michael cascade to construct the B-ring; and (3) an unprecedented stereocontrol intermolecular o -QM type [4 + 2]-cycloaddition to rapidly assemble core structure of rubriflordilactone A.
Topics & Concepts
ChemistryStereocenterIntramolecular forceRing (chemistry)Intermolecular forceCycloadditionStereochemistryCascadeTotal synthesisPrins reactionEnantioselective synthesisMoleculeOrganic chemistryCatalysisChromatographyPlant-derived Lignans Synthesis and BioactivityMagnolia and Illicium researchSynthetic Organic Chemistry Methods