One-Carbon Insertion and Polarity Inversion Enabled a Pyrrole Strategy to the Total Syntheses of Pyridine-Containing <i>Lycopodium</i> Alkaloids: Complanadine A and Lycodine
Donghui Ma, Brandon S. Martin, Katelyn S. Gallagher, Takeru Saito, Mingji Dai
Abstract
-Markovnikov hydroazidation, a Mukaiyama-Michael addition, and a Paal-Knorr pyrrole synthesis. Lycodine and complanadine A were prepared in 8 and 11 steps, respectively, from a readily available known compound.
Topics & Concepts
ChemistryPyridinePyrroleTotal synthesisImineStereochemistryOrganic chemistryCatalysisCholinesterase and Neurodegenerative DiseasesChemical synthesis and alkaloidsPlant Toxicity and Pharmacological Properties