Organic Letters
Letter
(6) (a) Gom
́
ez, L.; Garrabou, X.; Joglar, J.; Bujons, J.; Parella, T.;
conformationally constrained iminocyclitols of the benzo-
pyrrolidizine and cyclohexapyrrolizidine type. This strategy
compares favorably with the chemical synthesis of bicyclic
pyrrolidizines that started from more elaborate chiral
polyhydroxylated pyrrolidine derivatives.12 The compounds
obtained in this work have not been previously described, and
their biological activity against commercial glycosidases is
currently in progress and will be reported in due course.
Vilaplana, C.; Cardona, P. J.; Clapes
6309. (b) Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella, T.;
Bujons, J.; Clapes
, P. Chem.Eur. J. 2010, 16, 10691. (c) Calveras, J.;
Casas, J.; Parella, T.; Joglar, J.; Clapes, P. Adv. Synth. Catal. 2007, 349,
1661.
(7) (a) Sayago, F. J.; Jimenez, A. I.; Cativiela, C. Tetrahedron:
Asymmetry 2007, 18, 2358. (b) Sayago, F. J.; Calaza, M. I.; Jimenez, A.
I.; Cativiela, C. Tetrahedron 2008, 64, 84. (c) Sayago, F. J.; Laborda, P.;
́
, P. Org. Biomol. Chem. 2012, 10,
́
́
Calaza, M. I.; Jimen
2011, 2011.
́
ez, A. I.; Cativiela, C. Eur. J. Org. Chem. 2011,
ASSOCIATED CONTENT
* Supporting Information
■
(8) Suau, T.; Alvaro, G.; Benaiges, M. D.; Lopez-Santin, J. Biotechnol.
Bioeng. 2006, 93, 48.
(9) (a) Gefflaut, T.; Blonski, C.; Perie, J.; Willson, M. Prog. Biophys.
Mol. Biol. 1995, 63, 301. (b) Fessner, W.-D.; Sinerius, G.; Schneider,
A.; Dreyer, M.; Schulz, G. E.; Badia, J.; Aguilar, J. Angew. Chem., Int. Ed.
1991, 30, 555. (c) Espelt, L.; Parella, T.; Bujons, J.; Solans, C.; Joglar,
S
General methodology and detailed experimental compound
synthesis, analytical data, copies of H, 13C NMR and two-
1
dimensional NMR experiments for all compounds. This
material is available free of charge via the Internet at http://
J.; Delgado, A.; Clapes
Bujons, J.; Parella, T.; Calveras, J.; Joglar, J.; Delgado, A.; Clapes
́
, P. Chem.Eur. J. 2003, 9, 4887. (d) Espelt, L.;
́
, P.
Chem.Eur. J. 2005, 11, 1392. (e) Dalby, A.; Dauter, Z.; Littlechild, J.
AUTHOR INFORMATION
Corresponding Author
■
A. Protein Sci. 1999, 8, 291.
(10) Kajimoto, T.; Chen, L.; Liu, K. K. C.; Wong, C.-H. J. Am. Chem.
Soc. 1991, 113, 6678.
(11) Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R.
D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T.
R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.;
Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.;
Dombroski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.;
Byrd, E. F. C.; Van, V. T.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa,
N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-
Gordon, M.; Pople, J. A. J. Comput. Chem. 2000, 21, 1532.
(12) (a) Carmona, A. T.; Whightman, R. H.; Robina, I.; Vogel, P.
Helv. Chim. Acta 2003, 86, 3066. (b) Tamayo, J. A.; Franco, F.; Lo Re,
D.; Sanchez-Cantalejo, F. J. Org. Chem. 2009, 74, 5679. (c) Izquierdo,
I.; Plaza, M. T.; Franco, F. Tetrahedron: Asymmetry 2004, 15, 1465.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the Spanish MINECO CTQ2009-
07359, CTQ2012-31605, CTQ2012-32436, and CTQ2010-
17436; Generalitat de Catalunya (2009 SGR 00281); and ERA-
IB MICINN, PIM2010EEI-00607 (EIB.10.012. MicroTechEnz-
́
(research group E40). The authors thank Dr. Ciril Jimeno
from IQAC-CSIC for his assistance in the DFT calculations.
REFERENCES
■
(1) (a) Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu,
H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R. Carbohydr.
Res. 1999, 316, 95. (b) Asano, N.; Kuroi, H.; Ikeda, K.; Kizu, H.;
Kameda, Y.; Kato, A.; Adachi, I.; Watson, A. A.; Nash, R. J.; Fleet, G.
W. J. Tetrahedron: Asymmetry 2000, 11, 1. (c) Heightman, T. D.;
Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (d) Vasella, A.;
Davies, G. J.; Bohm, M. Curr. Opin. Chem. Biol. 2002, 6, 619.
(e) Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R.
J. Phytochemistry 2001, 56, 265. (f) Butters, T. D.; Dwek, R. A.; Platt,
F. M. Curr. Top. Med. Chem. 2003, 3, 561. (g) Oikonomakos, N. G.;
Tiraidis, C.; Leonidas, D. D.; Zographos, S. E.; Kristiansen, M.; Jessen,
C. U.; Norskov-Lauritsen, L.; Agius, L. J. Med. Chem. 2006, 49, 5687.
(h) Lahiri, R.; Ansari, A. A.; Vankar, Y. D. Chem. Soc. Rev. 2013, 42,
5102. (i) García-Moreno, M. I.; Rodríguez-Lucena, D.; Mellet, C. O.;
́
García Fernandez, J. M. J. Org. Chem. 2004, 69, 3578.
(2) (a) Blount, K. F.; Zhao, F.; Hermann, T.; Tor, Y. J. Am. Chem.
Soc. 2005, 127, 9818. (b) Alfonso, P.; Andreu, V.; Pino-Angeles, A.;
Moya-Garcia, A. A.; Garcia-Moreno, M. I.; Rodriguez-Rey, J. C.;
Sanchez-Jimenez, F.; Pocovi, M.; Mellet, C. O.; Fernandez, J. M. G.;
Giraldo, P. ChemBioChem 2013, 14, 943. (c) Sanchez-Fernandez, E.
M.; Risquez-Cuadro, R.; Mellet, C. O.; Fernandez, J. M. G.; Nieto, P.
M.; Angulo, J. Chem.Eur. J. 2012, 18, 8527. (d) Cativiela, C.; Díaz-
de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645. (e) Cativiela,
C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569.
(f) Cativiela, C.; Ordonez, M. Tetrahedron: Asymmetry 2009, 20, 1.
́
̃
(3) Gross, S.; Reissig, H.-U. Org. Lett. 2003, 5, 4305.
(4) Nicolaou, K. C.; Roecker, A. J.; Pfefferkorn, J. A.; Cao, G.-Q. J.
Am. Chem. Soc. 2000, 122, 2966.
(5) (a) Jones, G. B.; Guzel, M.; Mathews, J. E. Tetrahedron Lett.
2000, 41, 1123. (b) Bass, P. D.; Gubler, D. A.; Judd, T. C.; Williams, R.
M. Chem. Rev. 2013, 113, 6816.
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