Cyclobutane Amino Acid Analogues of Furanomycin Obtained by a Formal [2+2] Cycloaddition Strategy Promoted by Methylaluminoxane

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Canal, N. 1
  4. Corzana, F. 1
  5. Peregrina, J.M. 1
  6. Pérez-Fernández, M. 1
  7. Rodríguez, F. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    GRID grid.119021.a

Journal:
Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2010

Volume: 75

Issue: 3

Pages: 545-552

Type: Article

Export: RIS
DOI: 10.1021/jo9025258 PMID: 20038109 SCOPUS: 2-s2.0-75749129442 WoS: 000273982900003 GOOGLE SCHOLAR

Metrics

Cited by

  • Scopus Cited by: 22 (12-06-2021)

Journal Citation Reports

  • Year 2010
  • Journal Impact Factor: 4.002
  • Best Quartile: Q1
  • Area: CHEMISTRY, ORGANIC Quartile: Q1 Rank in area: 8/56 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2010
  • SJR Journal Impact: 2.127
  • Best Quartile: Q1
  • Area: Organic Chemistry Quartile: Q1 Rank in area: 16/174

Abstract

(Chemical Equation Presented) The synthesis and conformational analysis of a new type of conformationally restricted R-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. © 2009 American Chemical Society.