G. W. Amarante et al. / Tetrahedron Letters 51 (2010) 2597–2599
2599
Hartwig, J. H.; Thelen, M.; Resen, A.; Janmey, P. A.; Nairn, A. C.; Aderem, A.
Nature 1992, 356, 618–622.
8. Sanchez, A. M.; Malagarie-Cazenave, S.; Olea, N.; Vara, D.; Cuevas, C.; Diaz-
Laviada, I. Eur. J. Pharmacol. 2008, 584, 237–245.
2001, 57, 6901–6908; (j) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S.
Chem. Commun. 2001, 2030–2031; (k) Masunari, A.; Ishida, E.; Trazzi, G.;
Almeida, W. P.; Coelho, F. Synth. Commun. 2001, 31, 2127–2136; (l) McCauley, J.
A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am.
Chem. Soc. 1998, 120, 7647–7648.
9. (a) Yun, J. M.; Sim, T. B.; Hahm, H. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68,
7675–7680; (b) Seguin, C.; Ferreira, F.; Botuha, C.; Chemla, F.; Perez-Luna, A. J.
Org. Chem. 2009, 74, 6986–6992; (c) Allepuz, A. C.; Badorrey, R.; Diaz-de-
Villegas, M. D.; Galvez, J. A. Eur. J. Org. Chem. 2009, 35, 6172–7168.
10. (a) Basavaiah, D.; Rao, K. V.; Redy, R. J. Chem. Soc. Rev. 2007, 36, 1581–1588; (b)
Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511–4574; (c) Almeida, W. P.; Coelho,
F. Quim. Nova 2001, 23, 98–101.
11. For some selected references related to the mechanistic aspects of this
reaction, see: (a) Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin,
M. N. Angew. Chem., Int. Ed. 2004, 43, 4330–4333; (b) Santos, L. S.; da Silveira
Neto, B. A.; Consorti, C. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Dupont, J.;
Eberlin, M. N. J. Phys. Org. Chem. 2006, 19, 731–736; (c) Aggarwal, V. K.; Fulford,
S. Y.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2005, 44, 1706–1708; (d) Robiette,
R.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2007, 129, 15513–15525; (e)
Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147–
150; (f) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem.
2005, 70, 3980–3987; (g) Roy, D.; Sunoj, R. B. Org. Lett. 2007, 9. 4873-4876; (h)
Amarante, G. W.; Milagre, H. M. S.; Vaz, B. G.; Ferreira, B. R. V.; Eberlin, M. N.;
Coelho, F. J. Org. Chem. 2009, 74, 3031–3037; (i) Amarante, G. W.; Benassi, M.;
Milagre, H. M. S.; Braga, A. A. C.; Maseras, F.; Eberlin, M. N.; Coelho, F. Chem.
Eur. J. 2009, 15, 12460–12469.
12. For some examples related to the use of MBH adducts in the total synthesis of
natural products and drugs, see: (a) Coelho, F.; Veronese, D.; Pavam, C. H.; de
Paula, V. I.; Buffon, R. Tetrahedron 2006, 62, 4563–4572; (b) Perez, R.; Veronese,
D.; Coelho, F.; Antunes, O. A. C. Tetrahedron Lett. 2006, 47, 1325–1328; (c)
Silveira, G. P. D.; Coelho, F. Tetrahedron Lett. 2005, 46, 6477–6481; (d) Reddy, L.
J.; Fournier, J. F.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2005, 7, 2699–2701; (e)
Almeida, W. P.; Coelho, F. Tetrahedron Lett. 2003, 44, 937–940; (f) Feltrin, M. A.;
Almeida, W. P. Synth. Commun. 2003, 33, 1141–1146; (g) Dunn, P. J.; Fournier, J.
F.; Hughes, M. L.; Searle, P. M.; Wood, A. S. Org. Process Res. Dev. 2003, 7, 244–
253; (h) Rossi, R. C.; Coelho, F. Tetrahedron Lett. 2002, 42, 2797–2800; (i)
Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P. Tetrahedron
13. Amarante, G. W.; Rezende, P.; Cavallaro, M.; Coelho, F. Tetrahedron Lett. 2008,
49, 3744–3748.
14. Porto, R. S.; Amarante, G. W.; Cavallaro, M.; Poppi, R. J.; Coelho, F. Tetrahedron
Lett. 2009, 50, 1184–1187.
15. Park, K.-S.; Kim, J.; Choo, H.; Chong, Y. Synlett 2007, 395–398.
16. (a) Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609–8612; (b) Coelho,
F.; Almeida, W. P.; Mateus, C. R.; Veronese, D.; Lopes, E. C. S.; Silveira, G. P. C.;
Rossi, R. C.; Pavam, C. H. Tetrahedron 2002, 58, 7437–7447.
17. Souza, R. O. M. A.; Souza, A. L. F.; Fernandez, T. L.; Silva, A. C.; Pereira, V. L. P.;
Esteves, P. M.; Vasconcellos, M. L. A. A.; Antunes, A. O. C. Lett. Org. Chem. 2008,
5, 379–382.
18. (a) Mendez-Andino, J.; Paquette, L. A. Adv. Synth. Catal. 2002, 344, 303–311; (b)
Shadakshari, U.; Nayak, S. K. Tetrahedron 2001, 57, 4599–4602; (c) Basavaiah,
D.; Suguna Hyma, R. Tetrahedron 1996, 52, 1253–1258.
19. Lebel, H.; Leogane, O. Org. Lett. 2006, 8, 5717–5720. and references cited
therein.
20. Liang, H. Synlett 2008, 2554–2555.
21. The diastereoselectivity was measured by 1H NMR analysis of crude reaction
mixture and the relative stereochemistry was confirmed by the formation of
the corresponding oxazolidinone, which was analysed by 1H NMR. The
coupling constant (J) between the CH–O and CH–N is 8.2 Hz, which is
compatible for a syn relationship. See: (a) Futagawa, S.; Inui, T.; Shiba, T. Bull.
Chem. Soc. Jpn. 1973, 46, 3308–3310; (b) Dias, L. C.; Fattori, J.; Perez, C. C.; de
Oliveira, V. M.; Aguilar, A. M. Tetrahedron 2008, 64, 5891–5903.
22. Spectral data for ( )-Spisulosine: IR (Film,
mmax): 3348, 3297, 2955, 2919, 2851,
1607, 1471 cmÀ1 1H NMR (250 MHz, CDCl3), d ppm: 3.39–3.47 (m, 1H), 2.88–
;
3.06 (m, 1H), 1.64–1.88 (sl, 3H), 1.20–1.40 (m, 28H), 1.01 (d, J = 6.5 Hz, 3H),
0.88 (t, J = 7.0 Hz, 3H); 13C NMR (62.5 MHz, CDCl3), d ppm: 74.7, 50.3, 32.4,
31.9, 29.8, 29.7, 29.6, 29.3, 26.2, 22.7, 16.8, 14.1. HRMS (ESI) Calcd for
C18H34ON [M+H]+ 286.3110; Found 286.3088.