title: Total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 using tandem oxa-electrocyclization/oxidation1.
abstract: [reaction: see text] The total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.
authors.affiliation: Department of Chemistry, Boston University, Massachusetts 02215, USA.
authors.forename: Andrew S
authors.initials: AS
authors.lastname: Kleinke
authors.forename: Chaomin
authors.initials: C
authors.lastname: Li
authors.forename: Nicolas
authors.initials: N
authors.lastname: Rabasso
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D015843:Serpins / Q000138:chemical synthesis* / Q000494:pharmacology; D014764:Viral Proteins / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D003512:Cyclohexanones; C476114:EI-1941-2; D004852:Epoxy Compounds; D015843:Serpins; D014764:Viral Proteins; C074641:interleukin-1beta-converting enzyme inhibitor