Synthesis of Functionalized 1H-Isochromene Derivatives via a Au-Catalyzed Domino Cycloisomerization/Reduction Approach

Organic Letters

Volumn 17, Issue 24, 2015, Pages 6126-6129

  Tomás Mendivil, Eder ^a   Starck, Jéroîme ^b   Ortuno, Jean Claude ^b   Michelet, Véronique ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84952683178     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b03146     Document Type: Article

References (88)

1. Moloney, M. G. Nat. Prod. Rep. 2002, 19, 597 10.1039/b103777n
2. Singh, I. P.; Bodiwala, H. S. Nat. Prod. Rep. 2010, 27, 1781 10.1039/c0np00025f
3. Gao, J.-M.; Yang, S.-X.; Qin, J.-C. Chem. Rev. 2013, 113, 4755 10.1021/cr300402y
4. De Angelis, M.; Stossi, F.; Waibel, M.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Bioorg. Med. Chem. 2005, 13, 6529 10.1016/j.bmc.2005.07.014
5. Brown, L. E.; Cheng, K. C. C.; Wei, W. G.; Yuan, P.; Dai, P.; Trills, R.; Ni, F.; Yuan, J.; MacArthur, R.; Guha, R.; Johnson, R. L.; Suc, X. Z.; Dominguez, M. M.; Snyder, J. K.; Beeler, A. B.; Schaus, S. E.; Inglese, J.; Porco, J. A., Jr. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6775 10.1073/pnas.1017666108
6. Wang, Y.; Shang, X.; Wang, S.; Mo, S.; Li, S.; Yang, Y.; Ye, F.; Shi, J.; He, L. J. Nat. Prod. 2007, 70, 296 10.1021/np060476h
7. Brown, C. W.; Liu, S.; Klucik, J.; Berlin, K. D.; Brennan, P. J.; Kaur, D.; Benbrook, D. M. J. Med. Chem. 2004, 47, 1008 10.1021/jm0303453
8. Trisuwan, K.; Khamthong, N.; Rukachaisirikul, V.; Phongpaichit, S.; Preedanon, S.; Sakayaroj, J. J. Nat. Prod. 2010, 73, 1507 10.1021/np100282k
9. Wang, W.; Li, T.; Milburn, R.; Yates, J.; Hinnant, E.; Luzzio, M. J.; Noble, S. A.; Attardo, G. Bioorg. Med. Chem. Lett. 1998, 8, 1579 10.1016/S0960-894X(98)00274-1
10. Shishido, Y.; Wakabayashi, H.; Koike, H.; Ueno, N.; Nukui, S.; Yamagishi, T.; Murata, Y.; Naganeo, F.; Mizutani, M.; Shimada, K.; Fujiwara, Y.; Sakakibara, A.; Suga, O.; Kusano, R.; Ueda, S.; Kanai, Y.; Tsuchiya, M.; Satake, M. Bioorg. Med. Chem. 2008, 16, 7193 10.1016/j.bmc.2008.06.047
11. Liu, M.; Xiao, H.-T.; He, H.-P.; Hao, X.-Y. Chem. Nat. Compd. 2008, 44, 588 10.1007/s10600-008-9142-8
12. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 9548 10.1021/jo201923d
13. Mancuso, R.; Mehta, S.; Gabriele, B.; Salerno, G.; Jenks, W. S.; Larock, R. C. J. Org. Chem. 2010, 75, 897 10.1021/jo902333y
14. Arigela, R. K.; Samala, S.; Mahar, R.; Shukla, S. K.; Kundu, B. J. Org. Chem. 2013, 78, 10476 10.1021/jo401929q
15. Lee, J.; Panek, J. S. Org. Lett. 2014, 16, 3320 10.1021/ol501329t
16. Yue, D.; Della Ca, N.; Larock, R. C. Org. Lett. 2004, 6, 1581 10.1021/ol049690s
17. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079 10.1021/cr0201068
18. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127 10.1021/cr020095i
19. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368 10.1002/anie.200300616
20. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285 10.1021/cr020085h
21. Shen, H. C. Tetrahedron 2008, 64, 3885 10.1016/j.tet.2008.01.081
22. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395 10.1021/cr050041j
23. Krause, N.; Belting, V.; Deutsch, C.; Erdsack, J.; Fan, H.-T.; Gockel, B.; Hoffmann-Röder, A.; Morita, N.; Volz, F. Pure Appl. Chem. 2008, 80, 1063 10.1351/pac200880051063
24. Genin, E.; Michelet, V. In The Chemistry of Organogold Compounds; Rappoport, Z.; Marek, I.; Liebman, J. F., Eds.; John Wiley & Sons: 2014; Vol. 17, p 901.
25. Asao, N.; Chan, C. S.; Takahashi, K.; Yamamoto, Y. Tetrahedron 2005, 61, 11322 10.1016/j.tet.2005.09.012
26. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764 10.1021/ja017366b
27. Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139 10.1021/jo049416b
28. Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496 10.1021/jo035016x
29. Wei, L.-L.; Wei, L.-M.; Pan, W.-B.; Wu, M.-J. Synlett 2004, 1497 10.1055/s-2004-829056
30. Gulias, M.; Rodriguez, J. R.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2003, 5, 1975 10.1021/ol0345632
31. Bhunia, S.; Wang, K.-C.; Liu, R.-S. Angew. Chem., Int. Ed. 2008, 47, 5063 10.1002/anie.200800826
32. Jha, R. R.; Aggarwal, T.; Verma, A. K. Tetrahedron Lett. 2014, 55, 2603 10.1016/j.tetlet.2014.02.103
33. Ouyang, B.; Yuan, J.; Yang, Q.; Ding, Q.; Peng, Y.; Wu, J. Heterocycles 2010, 82, 1239 10.3987/COM-10-S(E)68
34. Tang, R.-Y.; Li, J.-H. Chem.-Eur. J. 2010, 16, 4733 10.1002/chem.201000133
35. Mariaule, G.; Newsome, G.; Toullec, P. Y.; Belmont, P.; Michelet, V. Org. Lett. 2014, 16, 4570 10.1021/ol5021256
36. Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953 10.1021/ol060645p
37. Yu, X.; Ding, Q.; Wang, W.; Wu, J. Tetrahedron Lett. 2008, 49, 4390 10.1016/j.tetlet.2008.05.009
38. Dyker, G.; Hildebrandt, D.; Liu, J.; Merz, K. Angew. Chem., Int. Ed. 2003, 42, 4399 10.1002/anie.200352160
39. Beeler, A. B.; Su, S.; Singleton, C. A.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129, 1413 10.1021/ja0674744
40. Leng, B.; Chichetti, S.; Su, S.; Beeler, A. B.; Porco, J. A., Jr. Beilstein J. Org. Chem. 2012, 8, 1338 10.3762/bjoc.8.153
41. For recent reactivity of carbonyl-yne derivatives with ammonium acetate, see: Domaradzki, M. E.; Long, Y.; She, Z.; Liu, X.; Zhang, G.; Chen, Y. J. Org. Chem. 2015, 80, doi 10.1021/acs.joc.5b01939.
42. Godet, T.; Vaxelaire, C.; Michel, C.; Milet, A.; Belmont, P. Chem.-Eur. J. 2007, 13, 5632 10.1002/chem.200700202
43. Dell'Acqua, M.; Facoetti, D.; Abbiati, G.; Rossi, E. Synthesis 2010, 2010, 2367 10.1055/s-0029-1218766
44. Dell'Acqua, M.; Castano, B.; Cecchini, C.; Pedrazzini, T.; Pirovano, V.; Rossi, E.; Caselli, A.; Abbiati, G. J. Org. Chem. 2014, 79, 3494 10.1021/jo5002559
45. Kotera, A.; Uenishi, J. I.; Uemura, M. Tetrahedron Lett. 2010, 51, 1166 10.1016/j.tetlet.2009.12.052
46. Liu, L.-P.; Hammond, G. B. Org. Lett. 2010, 12, 4640 10.1021/ol101985d
47. Bacchi, A.; Costa, M.; Della Ca, N.; Fabbricatore, M.; Fazio, A.; Gabriele, B.; Nasi, C.; Salerno, G. Eur. J. Org. Chem. 2004, 2004, 574 10.1002/ejoc.200300577
48. Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462 10.1021/jo070615f
49. Parker, E.; Leconte, N.; Godet, T.; Belmont, P. Chem. Commun. 2011, 47, 343 10.1039/C0CC02623A
50. Bantreil, X.; Vaxelaire, C.; Godet, T.; Parker, E.; Sauer, C.; Belmont, P. Org. Biomol. Chem. 2011, 9, 4831 10.1039/c1ob05354j
51. For an enantioselective version, see: Handa, S.; Slaughter, L. M. Angew. Chem., Int. Ed. 2012, 51, 2912 10.1002/anie.201107789
52. Nanayakkara, Y. S.; Woods, R. M.; Breitbach, Z. S.; Handa, S.; Slaughter, L. M.; Armstrong, D. W. J. Chromatograph. A 2013, 1305, 94 10.1016/j.chroma.2013.06.044
53. Terada, M.; Li, F.; Toda, Y. Angew. Chem., Int. Ed. 2014, 53, 235 10.1002/anie.201307371
54. Saito, K.; Kajiwara, Y.; Akiyama, T. Angew. Chem., Int. Ed. 2013, 52, 13284 10.1002/anie.201308303
55. Antoniotti, S.; Genin, E.; Michelet, V.; Geneît, J.-P. J. Am. Chem. Soc. 2005, 127, 9976 10.1021/ja0530671
56. Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Geneît, J.-P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112 10.1021/ja056857j
57. Neatu, F.; Li, Z.; Richards, R.; Toullec, P. Y.; Geneît, J.-P.; Dumbuya, K.; Gottfried, J. M.; Steinrück, H.-P.; Paîrvulescu, V. I.; Michelet, V. Chem.-Eur. J. 2008, 14, 9412 10.1002/chem.200801327
58. Toullec, P. Y.; Genin, E.; Antoniotti, S.; Geneît, J.-P.; Michelet, V. Synlett 2008, 2008, 707 10.1055/s-2008-1032108
59. Tomás-Mendivil, E.; Toullec, P. Y.; Diez, J.; Conejero, S.; Michelet, V.; Cadierno, V. Org. Lett. 2012, 14, 2520 10.1021/ol300811e
60. Tomás-Mendivil, E.; Toullec, P. Y.; Borge, J.; Conejero, S.; Michelet, V.; Cadierno, V. ACS Catal. 2013, 3, 3086 10.1021/cs4009144
61. Arcadi, A.; Pietropaolo, E.; Alvino, A.; Michelet, V. Org. Lett. 2013, 15, 2766 10.1021/ol401098b
62. Arcadi, A.; Pietropaolo, E.; Alvino, A.; Michelet, V. Beilstein J. Org. Chem. 2014, 10, 449 10.3762/bjoc.10.42
63. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46 10.1002/anie.200300626
64. Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology; Trabocchi, A., Ed.; John Wiley & Sons: New-York, 2013.
65. For a recent review dealing with HEH application, see: Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498 10.1039/c1cs15268h
66. Modern Gold Catalyzed Synthesis; Hashmi, A. S. K.; Toste, F. D., Eds.; Wiley-VCH: Weinheim, 2012.
67. Gold Catalysis: An Homogeneous Approach; Toste, F. D.; Michelet, V., Eds.; Imperial College Press: London, 2014.
68. The structure was confirmed by standard NMR analysis: Wang, X.; Dong, S.; Yao, Z.; Feng, L.; Daka, P.; Wang, H.; Xu, Z. Org. Lett. 2014, 16, 22 10.1021/ol4033286
69. 4NF-catalyzed 5-exo cycloisomerization process for ortho-alkynylbenzylalcohols, see: Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697 10.1016/S0040-4020(01)00991-7
70. Hashmi, A. S. K.; Weyraugh, J. P.; Rudolph, M.; Kupejovic, E. Angew. Chem., Int. Ed. 2004, 43, 6545 10.1002/anie.200460232
71. Hashmi, A. S. K.; Kurpejović, E.; Wölfle, M.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2007, 349, 1743 10.1002/adsc.200600653
72. Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274 10.1021/ja066220f
73. Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244 10.1021/ja803890t
74. Fustero, S.; Ibanez, I.; Barrio, P.; Maestro, M. A.; Catalan, S. Org. Lett. 2013, 15, 832 10.1021/ol3035142
75. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062 10.1002/anie.201107017
76. Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments; Molnar, A., Ed.; Wiley-VCH: 2013.
77. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2nd, completely revised and enlarged ed.; Wiley-VCH: Weinheim, 2013.
78. Bright, T. V.; Dalton, F.; Elder, V.-L.; Murphy, C. D.; O'Connor, N. K.; Sandford, G. Org. Biomol. Chem. 2013, 11, 1135 10.1039/c2ob27140k
79. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308 10.1039/B711844A
80. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320 10.1039/B610213C
81. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359 10.1021/jm800219f
82. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432 10.1021/cr4002879
83. For Diels-Alder cycloadditions, see: Sanjuan, A. M.; Garcia-Garcia, P.; Fernandez-Rodriguez, M. A.; Sanz, R. Adv. Synth. Catal. 2013, 355, 1955 10.1002/adsc.201300448
84. A deactivation of the gold catalyst may explain the nonreactivity of 1f according to a recent desilylation reaction: Hooper, T. N.; Green, M.; Russell, C. A. Chem. Commun. 2010, 46, 2313 10.1039/b923900f
85. Similar reactivity of 1g was observed for Pd- and Ag-catalyzed cycloisomerization/functionalization processes; see refs 5b and 6c.
86. Li, X.; Chianese, A. R.; Vogel, T.; Crabtree, R. H. Org. Lett. 2005, 7, 5437 10.1021/ol052186i
87. Dell'Acqua, M.; Facoetti, D.; Abbiati, G.; Rossi, E. Synthesis 2010, 2010, 2367 10.1055/s-0029-1218766
88. Smith, R. E.; Richards, N. G. J. J. Org. Chem. 1997, 62, 1183 10.1021/jo961496z