title: Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddition strategy promoted by methylaluminoxane.
abstract: The synthesis and conformational analysis of a new type of conformationally restricted alpha-amino acid analogue of the amino acid antibiotic furanomycin is presented. The restriction involves the cis-fused cyclobutane and tetrahydrofuran units, generating the unusual 2-oxabicyclo[3.2.0]heptane core, which is found in a great number of biologically active natural products. The synthetic strategy is based on a formal [2 + 2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes and 2,3-dihydrofuran as a donor alkene, promoted by bulky aluminum-derived Lewis acids, particularly by methylaluminoxane (MAO). Additionally, following the same strategy, the synthesis of furanomycin analogues incorporating the 2-oxabicyclo[4.2.0]octane is reported.
authors.affiliation: Departamento de Quimica, Universidad de La Rioja, Grupo de Sintesis Quimica de La Rioja, U.A.-C.S.I.C., E-26006 Logrono, Spain. alberto.avenoza@unirioja.es
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.forename: Noelia
authors.initials: N
authors.lastname: Canal
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
authors.forename: Marta
authors.initials: M
authors.lastname: Pérez-Fernández
authors.forename: Fernando
authors.initials: F
authors.lastname: Rodríguez
mesh_terms: D017607:Aluminum Compounds / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D017607:Aluminum Compounds; D000596:Amino Acids; D003503:Cyclobutanes; C063753:furanomycin