Total Synthesis of <i>ent</i>-Plagiochianin B
Richard K. Jackson, John L. Wood
Abstract
An enantioselective total synthesis of plagiochianin B is described that employs (+)-3-carene as its point of departure and delivers the enantiomer of the natural product. Key features of the synthesis include a palladium-mediated regioselective oxidative cleavage of an olefin residing on a pyridine derived from a 6π-azatriene electrocyclization.
Topics & Concepts
ChemistryTotal synthesisRegioselectivityEnantiomerEnantioselective synthesisOlefin fiberOxidative cleavagePyridineNatural productStereochemistryPalladiumCleavage (geology)Combinatorial chemistryOrganic chemistryCatalysisGeotechnical engineeringEngineeringFracture (geology)Marine Sponges and Natural ProductsTraditional and Medicinal Uses of AnnonaceaeCatalytic C–H Functionalization Methods