title: Multicomponent macrocyclization reactions (MCMRs) employing highly reactive acyl ketene and nitrile oxide intermediates.
abstract: An efficient synthesis of spiro-fused macrolactams by a multicomponent macrocyclization reaction (MCMR) is reported. The use of highly reactive, transient intermediates in this MCMR permits short reaction times, even at high dilution. The methods employed for this MCMR were first developed as a four-component strategy for the synthesis of β-ketoamide isoxazolines and a new macrocyclization reaction is reported.
authors.affiliation: Department of Chemistry, University of California, Davis, 1 Shields Avenue, Davis, California 95616, USA.
authors.forename: John M
authors.initials: JM
authors.lastname: Knapp
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005030:Ethylenes; D007659:Ketones; D047029:Lactams, Macrocyclic; D009570:Nitriles; D010087:Oxides; D013141:Spiro Compounds; C008223:ketene