title: A short stereoselective synthesis of racemic 2-epicalvine.
abstract: The cycloaddition reaction of 6-pentyl-3,4,5,6-tetrahydropyridine 1-oxide with butyl vinyl ether was used as a key step in the short stereoselective racemic synthesis of ladybird beetle alkaloid, 2-epicalvine. The cycloadduct was subjected to quatemization with 2-bromoethanol, followed by ring opening and lactonization to afford the natural product in a one-pot reaction.
authors.affiliation: Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia.
authors.forename: Basem A
authors.initials: BA
authors.lastname: Moosa
authors.forename: Shaikh A
authors.initials: SA
authors.lastname: Ali
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C552822:2-epicalvine; D000470:Alkaloids; D010880:Piperidines