Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddition strategy promoted by methylaluminoxane.
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.
Avenoza
Alberto
A
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
Busto
Jesús H
JH
Canal
Noelia
N
Corzana
Francisco
F
Peregrina
Jesús M
JM
Pérez-Fernández
Marta
M
Rodríguez
Fernando
F
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
D017607:Aluminum Compounds; D000596:Amino Acids; D003503:Cyclobutanes; C063753:furanomycin