Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition
Yuzhou Wang, André Hennig, Thomas Küttler, Christian Hahn, Anne Jäger, Peter Metz
Abstract
Using an intramolecular nitrone cycloaddition and a Heck cyclization as the crucial transformations, a total synthesis of the racemic morphine alkaloid thebainone A was accomplished in 22 steps commencing with isovanillin.
Topics & Concepts
NitroneChemistryIntramolecular forceCycloadditionTotal synthesisAlkaloidStereochemistryOrganic chemistryCatalysisAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsTraditional and Medicinal Uses of Annonaceae