PDF herunterladen
Synthesis 2010(1): 110-114  
DOI: 10.1055/s-0029-1217085
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoenzymatic Synthesis of Substituted 1H-Inden-1-ones Using Lipases

Ana Rioz-Martínez, Gonzalo de Gonzalo, Vicente Gotor*
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006 Oviedo, Spain
Fax: +34(98)5103448; e-Mail: vgs@fq.uniovi.es;
Weitere Informationen

Publikationsverlauf

Received 30 July 2009
Publikationsdatum:
26. Oktober 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A practical and straightforward chemoenzymatic synthesis of novel acetoxy- and hydroxy-1H-inden-1-ones starting from commercial indan-1-ones is described. By using different lipases, the final step of the preparation can be performed with high conversion working under mild reaction conditions. The desired compounds, which present a great interest since they can be employed as target substrates in enzymatic activity detection assays, were obtained in good overall yields.

Key words

enzymes - elimination - hydrolyses - ketones - fluorogenic compounds

    References

  • 1a Reetz MT. Angew. Chem. Int. Ed.  2001,  40:  284 
    Suche in Google Scholar
  • 1b Goddard JP. Reymond JL. Trends Biotechnol.  2004,  22:  363 
    Suche in Google Scholar
  • 1c Reymond JL. Enzyme Assays: High-throughput Screening, Genetic Selection and Fingerprinting   Wiley-VCH; Weinheim: 2006. 
  • 1d Reymond JL. Fluxà V. Maillard N. Chem. Commun.  2009,  34 
  • See for example:
  • 2a List B. Barbas CF. Lerner RA. Proc. Natl. Acad. Sci. U.S.A.  1998,  35:  15351 
    Suche in Google Scholar
  • 2b Badalassi F. Wahler D. Klein G. Crotti P. Reymond JL. Angew. Chem. Int. Ed.  2000,  39:  4067 
    Suche in Google Scholar
  • 2c Sevestre A. Helanie V. Guyot G. Martin C. Hecquet L. Tetrahedron Lett.  2003,  44:  827 
    Suche in Google Scholar
  • 2d Kofoed J. Darbre T. Reymond JL. Chem. Commun.  2006,  1482 
  • 3 Gonçalves MST. Chem. Rev.  2009,  109:  190 
    CrossrefSuche in Google Scholar
  • 4a Webb MR. Corrie JET. Biophys. J.  2001,  81:  1562 
    Suche in Google Scholar
  • 4b Berthelot T. Lain G. Latxague L. Déleris G. J. Fluoresc.  2004,  14:  671 
    Suche in Google Scholar
  • 4c Kosiova I. Janícova A. Kois P. Beilstein J. Org. Chem.  2006,  2:  2 
    Suche in Google Scholar
  • For some recent reviews on BVMOs:
  • 5a Mihovilovic MD. Curr. Org. Chem.  2006,  10:  1265 
    Suche in Google Scholar
  • 5b Torres Pazmiño DE. Fraaije MW. In Future Directions in Biocatalysis   Matsuda T. Elsevier; Dordrecht: 2007.  p.107 
  • 5c Kayser MM. Tetrahedron  2009,  65:  947 
    Suche in Google Scholar
  • 6 Sicard R. Chen LS. Marsaioli AJ. Reymond JL. Adv. Synth. Catal.  2005,  347:  1041 
    CrossrefSuche in Google Scholar
  • 7a de Gonzalo G. Torres Pazmiño DE. Ottolina G. Fraaije MW. Carrea G. Tetrahedron: Asymmetry  2006,  17:  130 
    Suche in Google Scholar
  • 7b Rodríguez C. de Gonzalo G. Torres Pazmiño DE. Fraaije MW. Gotor V. Tetrahedron: Asymmetry  2007,  18:  1338 
    Suche in Google Scholar
  • 7c Rodríguez C. de Gonzalo G. Torres Pazmiño DE. Fraaije MW. Gotor V. Tetrahedron: Asymmetry  2008,  19:  197 
    Suche in Google Scholar
  • 8 Minuti L. Taticchi A. Marrocchi A. Lanari D. Broggi A. Gacs-Baitz E. Tetrahedron: Asymmetry  2003,  14:  481 
    CrossrefSuche in Google Scholar
  • 9 To see the protocol for the benzylic bromination of the indan-1-one: Podgoršek A. Stavber S. Zupan M. Iskra J. Tetrahedron Lett.  2006,  47:  1097 
    CrossrefSuche in Google Scholar
  • 10 Zimmerman H. Suryanarayan V. Eur. J. Org. Chem.  2007,  4091 
    Crossref
  • 11a Ghanem A. Tetrahedron  2007,  63:  1721 
    Suche in Google Scholar
  • 11b Gotor V. Alfonso I. García-Urdiales E. Asymmetric Organic Synthesis with Enzymes   Wiley-VCH; Weinheim: 2008. 
  • For some recent examples, see:
  • 12a Belleza F. Cipiciani A. Ricci G. Ruzziconi R. Tetrahedron  2005,  61:  8005 
    Suche in Google Scholar
  • 12b Majewska P. Kafarski P. Lejczak B. Tetrahedron: Asymmetry  2006,  17:  2870 
    Suche in Google Scholar
  • 12c Palomo JM. Filice M. Fernández-Lafuente R. Terreni M. Guisán JM. Adv. Synth. Catal.  2007,  349:  1969 
    Suche in Google Scholar
  • 12d Recuero V. Brieva R. Gotor V. Tetrahedron: Asymmetry  2008,  19:  1684 
    Suche in Google Scholar
  • 12e Yu LJ. Xu Y. Yu XW. J. Mol. Catal. B: Enzym.  2009,  57:  23 
    Suche in Google Scholar