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Synthesis 2010(1): 110-114
DOI: 10.1055/s-0029-1217085
DOI: 10.1055/s-0029-1217085
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Chemoenzymatic Synthesis of Substituted 1H-Inden-1-ones Using Lipases
Further Information
Received
30 July 2009
Publication Date:
26 October 2009 (online)
Publication History
Publication Date:
26 October 2009 (online)
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
-
1a
Reetz MT. Angew. Chem. Int. Ed. 2001, 40: 284 -
1b
Goddard JP.Reymond JL. Trends Biotechnol. 2004, 22: 363 -
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 -
2b
Badalassi F.Wahler D.Klein G.Crotti P.Reymond JL. Angew. Chem. Int. Ed. 2000, 39: 4067 -
2c
Sevestre A.Helanie V.Guyot G.Martin C.Hecquet L. Tetrahedron Lett. 2003, 44: 827 -
2d
Kofoed J.Darbre T.Reymond JL. Chem. Commun. 2006, 1482 - 3
Gonçalves MST. Chem. Rev. 2009, 109: 190 -
4a
Webb MR.Corrie JET. Biophys. J. 2001, 81: 1562 -
4b
Berthelot T.Lain G.Latxague L.Déleris G. J. Fluoresc. 2004, 14: 671 -
4c
Kosiova I.Janícova A.Kois P. Beilstein J. Org. Chem. 2006, 2: 2 - For some recent reviews on BVMOs:
-
5a
Mihovilovic MD. Curr. Org. Chem. 2006, 10: 1265 -
5b
Torres Pazmiño DE.Fraaije MW. In Future Directions in BiocatalysisMatsuda T. Elsevier; Dordrecht: 2007. p.107 -
5c
Kayser MM. Tetrahedron 2009, 65: 947 - 6
Sicard R.Chen LS.Marsaioli AJ.Reymond JL. Adv. Synth. Catal. 2005, 347: 1041 -
7a
de Gonzalo G.Torres Pazmiño DE.Ottolina G.Fraaije MW.Carrea G. Tetrahedron: Asymmetry 2006, 17: 130 -
7b
Rodríguez C.de Gonzalo G.Torres Pazmiño DE.Fraaije MW.Gotor V. Tetrahedron: Asymmetry 2007, 18: 1338 -
7c
Rodríguez C.de Gonzalo G.Torres Pazmiño DE.Fraaije MW.Gotor V. Tetrahedron: Asymmetry 2008, 19: 197 - 8
Minuti L.Taticchi A.Marrocchi A.Lanari D.Broggi A.Gacs-Baitz E. Tetrahedron: Asymmetry 2003, 14: 481 - 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 - 10
Zimmerman H.Suryanarayan V. Eur. J. Org. Chem. 2007, 4091 -
11a
Ghanem A. Tetrahedron 2007, 63: 1721 -
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 -
12b
Majewska P.Kafarski P.Lejczak B. Tetrahedron: Asymmetry 2006, 17: 2870 -
12c
Palomo JM.Filice M.Fernández-Lafuente R.Terreni M.Guisán JM. Adv. Synth. Catal. 2007, 349: 1969 -
12d
Recuero V.Brieva R.Gotor V. Tetrahedron: Asymmetry 2008, 19: 1684 -
12e
Yu LJ.Xu Y.Yu XW. J. Mol. Catal. B: Enzym. 2009, 57: 23