title: Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization.
abstract: The Michael-Claisen domino (MCD) cyclization used in the lycopodine synthesis by Stork, was evaluated mechanistically using DFT calculations. Calculations suggest that a dianion is not formed, which conforms to classical dianion formation normally requiring strong kinetic bases. Instead ethoxide in ethanol produces a monoanionic species driving the MCD cyclization. This endeavor has opened up potential to expand the scope of this unique reaction and provide educational clarity.
authors.affiliation: School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia.
authors.forename: Wilhelm A
authors.initials: WA
authors.lastname: Eger
authors.forename: Ernst
authors.initials: E
authors.lastname: Anders
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D003500:Cyclization; D008956:Models, Chemical; D008958:Models, Molecular; D011807:Quinolizines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D011807:Quinolizines; C016542:lycopodine