Highly functionalized spirocyclohexadienones from Morita-Baylis-Hillman adducts

Synlett

Volumn , Issue 14, 2009, Pages 2333-2337

  Pirovani, Rodrigo V ^a   Ferreira, Bruno R V ^a   Coelho, Fernando ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Heck reaction; Hypervalent iodine; Morita Baylis Hillman; Palladacycles; Spiro compounds

Indexed keywords

1,4 CYCLOHEXADIENE; ANNOSQUALINE; FUTOENONE; INTERIORIN A; IODINE; NATURAL PRODUCT; PHENOL DERIVATIVE; SPIROCYCLOHEXADIENONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNONA; ANNONA SQUAMOSA; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; HAIFENTENG; HECK REACTION; KADSURA; KADSURA INTERIOR; MOLECULAR INTERACTION; MORITA BAYLIS HILLMAN ADDUCT REACTION; NONHUMAN; OXIDATION; PIPERACEAE; PRODUCT RECOVERY; STRUCTURE ANALYSIS;

EID: 69449087050     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217725     Document Type: Article

References (74)

1. For an example of a marine natural products having a spiro hexadienone moiety, see: Beil, W.; Jones, P. G.; Nerenz, F.; Winterfeldt, E. Tetrahedron 1998, 54, 7273; and references cited therein.
2. For the isolation of annosqualine, see: (a) Yang, Y.-L.; Chang, F.-R.; Wu, Y.-C. Helv. Chim. Acta 2004, 87, 1392.
3. (b) For the total synthesis (±)-annosqualine, see: Shigehisa, H.; Takayama, J.; Honda, T. Tetrahedron Lett. 2006, 47, 7301.
4. For isolation, structure determination and synthesis of futoenone, see: (a) Ogiso, A.; Kurabayashi, M.; Mishima, H.; Woods, M. C. Tetrahedron Lett. 1968, 16, 2003.
5. (b) Woods, M. C.; Miura, I.; Ogiso, A.; Kurabayashi, M.; Mishima, H. Tetrahedron Lett. 1968, 16, 2009.
6. (c) Ogiso, A.; Kurabayashi, M.; Takahashi, S.; Mishima, H.; Woods, M. C. Chem. Pharm. Bull. 1970, 18, 105 .
7. For the X-ray data of futoenone, see: (d) Song, D.; Billodeaux, D. R.; Fronczek, F. R.; Fischer, N. H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2001, 57, 1094.
8. (e) Ponpipom, M. M.; Yue, B. Z.; Bugianesi, R. L.; Brokker, D. R.; Chang, M. N.; Shen, T. Y. Tetrahedron Lett. 1986, 27, 309.
9. For an example concerning the total synthesis of futoenone, see: (f) Angle, S. R.; Turnbull, K. D. J. Org. Chem. 1993, 58, 5360.
10. Yeh, L.-A.; Chen, J.; Baculi, F.; Gingrich, D. E.; Shen, T. Y. Bioorg. Med. Chem. Lett. 1995, 5, 1637.
11. (a) Lin, L.-C.; She, C.-C.; Chen, Y.-C.; Tsai, T.-H. J. Nat. Prod. 2006, 69, 842.
12. (b) Shen, T. Y. Lipids 1991, 26, 1154.
13. (a) Chen, D.-F.; Zhang, S.-X.; Kozuka, M.; Sun, Q.-Z.; Feng, J.; Wang, Q.; Mukainaka, T.; Nobukuni, Y.; Tokuda, H.; Nishino, H.; Wang, H.-K.; Morris-Natschke, S. L.; Lee, K.-H. J. Nat. Prod. 2002, 65, 1242.
14. (b) Green, S. P.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 193.
15. (a) Sandin, P.; Martinez-Grau, A.; Sánchez, L.; Seoane, C.; Pou-Américo, R.; Orti, E.; Martín, N. Org. Lett. 2005, 7, 295.
16. (b) For an example about the fungicide activity of spirocyclohexadienone compounds, see: Tsuge, O.; Kanemasa, S.; Watanabe, H. JP 61178903, 1987; Chem. Abstr. 1987, 106, 135175.
17. For an outstanding example, see: de Turiso, F. G.-L.; Curran, D. P. Org. Lett. 2005, 7, 151; and references cited therein.
18. Appel, T. R.; Yehia, N. A. M.; Baumeister, U.; Hartung, H.; Kluge, R.; Ströhl, D.; Fanghänel, E. Eur. J. Org. Chem. 2003, 47.
19. Wulff, W. D.; Gilbertson, S. R. J. Am. Chem. Soc. 1985, 107, 503.
20. Nifontov, Y. V.; Glushkov, G. A.; Shklyaev, Y. V. Russ. Chem. Bull. Int. Ed. 2003, 52, 437.
21. Catellani, M.; Cugini, F.; Bocelli, G. J. Organomet. Chem. 1999, 584, 63.
22. (a) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
23. (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299; and references cited therein.
24. For some outstanding examples of the use of β-keto esters as building block in organic synthesis, see: (a) LuoJ, ; Xu, L.-W.; Hay, R. A. S.; Lu, Y. Org. Lett. 2008, 11, 437.
25. (b) Maity, P.; Lepore, S. D. J. Org. Chem. 2009, 74, 158.
26. (c) KatritzkyA, R.; Wang, Z.; Wang, M.; Wilkerson, C. R.; Hall, C. D.; Akhmedov, N. G. J. Org. Chem. 2004, 69, 6617.
27. (d) Ismabery, N.; Lavila, R. Chem. Eur. J. 2008, 14, 8444.
28. (e) Shestopalov, A. N.; Shestopalov, A. A.; Rodinovskaya, L. A. Synlett 2008, 1.
29. (f) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 24, 4957.
30. (g) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
31. For some recent examples concerning the utilization of Baylis-Hillman adduct as substrate for the synthesis of natural products and drugs, see: (a) Mateus, C. R.; Coelho, F. J. Braz. Chem. Soc. 2005, 16, 386; available free of charge at http://jbcs.sbq.org.br/online/2005/vol16-n3A/11-238-04.pdf.
32. (b) Porto, R. S.; Coelho, F. Synth. Commun. 2004, 34, 3037.
33. (c) Feltrin, M. A.; Almeida, W. P. Synth. Commun. 2003, 33, 1141.
34. (d) Rossi, R. C.; Coelho, F. Tetrahedron Lett. 2002, 42, 2797.
35. (e) Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P. Tetrahedron 2001, 57, 6901.
36. (f) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030.
37. (g) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867.
38. (h) Masunari, A.; Trazzi, G.; Ishida, E.; Coelho, F.; Almeida, W. P. Synth. Commun. 2001, 31, 2127.
39. For recent discussions about the mechanism of MBH reaction, see: (a) Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147.
40. (b) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980.
41. (c) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem. Int. Ed. 2005, 44, 1706.
42. (d) Robiette, R.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2007, 129, 15513.
43. (e) Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem. Int. Ed. 2004, 43, 4330.
44. (f) Amarante, G. W.; Benassi, M.; Sabino, A. A.; Esteves, P. M.; Coelho, F.; Eberlin, M. N. Tetrahedron Lett. 2006, 47, 8427.
45. (g) Santos, L. S.; 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.
46. (h) Amarante, G. W.; Milagre, H. M. S.; Gontigo, B. V.; Ferreira, B. R. V.; Eberlin, M. N.; Coelho, F. J. Org. Chem. 2009, 74, 3031.
47. For some outstanding examples of intermolecular-intramolecular palladium-mediated Heck-type reaction of MBH adducts, see: (a) Basavaiah, D.; Muthukumaran, K. Tetrahedron 1998, 54, 4943.
48. (b) Sundar, N.; Bhat, S. V. Synth. Commun. 1998, 28, 2311.
49. (c) Kumareswaran, R.; Vankar, Y. D. Synth. Commun. 1998, 28, 2291.
50. (d) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373.
51. (e) Kabalka, G. W.; Venkataiah, B.; Dong, G. Org. Lett. 2003, 5, 3803.
52. (f) Perez, R.; Veronese, D.; Coelho, F.; Antunes, O. A. C. Tetrahedron Lett. 2006, 47, 1325.
53. (g) Kim, J. M.; Kim, K. H.; Kim, T. H. J. N. Tetrahedron Lett. 2008, 49, 3248.
54. (h) Lee, H. S.; Kim, S. H.; Gowrisankar, S.; Kim, J. N. Tetrahedron 2008, 64, 7183.
55. (i) Coelho, F.; Veronese, D.; Pavam, C. H.; De Paula, V. I.; Buffon, R. Tetrahedron 2006, 62, 4563.
56. (j) Vasudevan, A.; Tseng, P.-S.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 8591.
57. (a) Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609.
58. (b) Coelho, F.; Almeida, W. P.; Veronese, D.; Mateus, C. R.; Lopes, E. C. S.; Rossi, R. C.; Silveira, G. P. C.; Pavam, C. H. Tetrahedron 2002, 62, 7437.
59. (a) Catellani, M.; Motti, E.; Della Ca', N. Acc. Chem. Res. 2008, 41, 1512.
60. (b) Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440.
61. (c) Phan, N. T. S.; Van der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 606.
62. (d) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
63. (e) Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
64. (f) Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055.
65. (g) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
66. (a) Alonso, D. A.; Botella, L.; Nájera, C.; Pacheco, C. Synthesis 2004, 1713.
67. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172.
68. (c) Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2002, 67, 5588.
69. Botella, L.; Nájera, C. J. Org. Chem. 2005, 70, 4630.
70. See Supporting Information for experimental details.
71. (a) Wang, K.; Fu, X.; Liu, J.; Liang, Y.; Dong, D. Org. Lett. 2009, 11, 1015; and references cited therein.
72. (b) White, J. D.; Caravatti, G.; Kline, T. B.; Edstrom, E. Tetrahedron 1983, 39, 2993.
73. (a) Caló, V.; Nacci, A.; Monopoli, A.; Ferola, V. J. Org. Chem. 2007, 72, 2596.
74. (b) See also: Pan, D.; Chen, A.; Su, Y.; Zhou, W.; Li, S.; Jia, W.; Xiao, J.; Liu, Q.; Zhang, L.; Jiao, N. Angew. Chem. Int. Ed. 2008, 47, 4729.