title: Assembly of a key dienic intermediate for tetrodotoxin via a Machetti-DeSarlo reaction.
abstract: A route to a racemic diene intermediate for the synthesis of tetrodotoxin is described. Key steps of the sequence leading to such a compound include the oxidative amidation of a phenol, a Cu(II)-catalyzed cyclocondensation of a nitroketone with an olefin (Machetti-DeSarlo reaction), and a nucleophilic fragmentation of the resulting isoxazoline. Several unusual reactions encountered in the course of this study are thoroughly discussed.
authors.affiliation: Department of Chemistry, The University of British Columbia , 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
authors.forename: Jaclyn
authors.initials: J
authors.lastname: Chau
authors.forename: Sanjia
authors.initials: S
authors.lastname: Xu
authors.forename: Marco A
authors.initials: MA
authors.lastname: Ciufolini
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D013779:Tetrodotoxin; D003300:Copper