Total Synthesis of Putative Melognine
Yui Irie, Satoshi Yokoshima
Abstract
2 reaction of a nosylamide. Enyne metathesis of the cyclic alkyne under an atmosphere of ethylene afforded a 1,3-diene. Intramolecular cycloaddition of a nitrone and an azomethine ylide with the 1,3-diene moiety constructed the characteristic highly fused skeleton. Further transformation, including ring-closing metathesis, resulted in the synthesis of melognine, whose NMR spectra did not match the reported data. Close inspection of the spectra of melognine in the literature suggested that the structure of melognine might be identical with that of a known alkaloid, melodinine L.
Topics & Concepts
ChemistryIntramolecular forceCycloadditionNitroneEnyne metathesisStereochemistryAlkyneDieneMoietyTotal synthesisYlideSN2 reactionEthyleneRing-closing metathesisAcyclic diene metathesisMetathesisOrganic chemistryPolymerizationCatalysisPolymerNatural rubberChemical synthesis and alkaloidsTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacology