Transition metals catalyzed C-C and C-O bonds formation: Facile synthesis of flavans and benzoxepines

Tetrahedron

Volumn 69, Issue 38, 2013, Pages 8305-8315

  Ramulu, B Venkat ^a   Mahendar, L ^a   Krishna, J ^a   Reddy, A Gopi Krishna ^a   Suchand, B ^a   Satyanarayana, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY HYDERABAD   (India)

Author keywords

Cu catalysis; Pd catalysis; Alcohols; Benzoxepines; Dihydrochalcones; Flavans

Indexed keywords

2 (1,3 BENZODIOXOL 5 YL) 2 METHYL 2,3,4,5 TETRAHYDRO 1 BENZOXEPINE; 2 (3,4 DIMETHOXYPHENYL) 2 ETHYLCHROMANE; 2 (3,4 DIMETHOXYPHENYL) 2 METHYLCHROMANE; 2 PHENYL 2,3,4,5 TETRAHYDRO 1 BENZOXEPINE; CARBON; COPPER; DIBENZOXEPIN DERIVATIVE; FLAVAN DERIVATIVE; OXYGEN; PALLADIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COVALENT BOND; CRYSTAL STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; X RAY DIFFRACTION;

EID: 84881185253     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.046     Document Type: Article

References (77)

1. A.F. Abdel-Razik, M.I. Nassar, E.D.A. El-Khrisy, A.A.M. Dawidar, and T.J. Mabry Fitoterapia 76 2005 762 764
2. T. Morikawa, F. Xu, H. Matsuda, and M. Yoshikawa Chem. Pharm. Bull. 54 2006 1530 1534
3. L.J. Li, Y. Zhang, P. Zhang, H.F. Pi, H.L. Ruan, and J.Z. Wu J. Asian Nat. Prod. Res. 13 2011 367 372
4. S.T. Saengchantara, and T.W. Wallace Nat. Prod. Rep. 3 1986 465 475
5. N.C. Veitch, and R.J. Grayer Nat. Prod. Rep. 28 2011 1626 1695
6. Y.-M. Cui, H. Wang, Q.-R. Liu, M. Han, Y. Lu, and C.-Q. Zhao Bioorg. Med. Chem. Lett. 21 2011 4400 4403
7. A. Numata, T. Takemura, H. Ohbayashi, T. Katsuno, K. Yamamoto, K. Sato, and S. Kobayashi Chem. Pharm. Bull. 31 1983 2146 2149
8. S. Ghosal, S.K. Singh, and R.S. Srivastava Phytochemistry 24 1985 151 153
9. D.J. Bauer, J.W.T. Selway, J.F. Batchelor, M. Tisdale, I.C. Caldwell, and D.A. Young Nature (London) 292 1981 369 370
10. X. Hu, J.-W. Wu, M. Wang, M.-H. Yu, Q.-S. Zhao, H.-Y. Wang, and A.-J. Hou J. Nat. Prod. 75 2012 82 87
11. B.A. Sutherland, R.M.A. Rahman, and I. Appleton J. Nutr. Biochem. 17 2006 291 306
12. H.-H.S. Chowa, and I.A. Hakima Pharm. Res. 64 2011 105 112
13. O. Kajimoto, Y. Kajimoto, M. Yabune, T. Nakamura, K. Kotani, Y. Suzuki, A. Nozawa, K. Nagata, T. Unno, Y.M. Sagesaka, T. Kakuda, and T. Yoshikawa J. Health Sci. 51 2005 161 171
14. M. Shimizu, Y. Shirakami, and H. Moriwaki Int. J. Mol. Sci. 9 2008 1034 1049
15. For isolation of ponapensin, see: A.A. Salim, A.D. Pawlus, H.-B. Chai, N.R. Farnsworth, A.D. Kinghorn, and E.J. Carcache-Blanco Bioorg. Med. Chem. Lett. 17 2007 109 112
16. For synthesis of ponapensin, see: N.J. Lajkiewicz, S.P. Roche, B. Gerard, and J.A. Porco J. Am. Chem. Soc. 134 2012 13108 13113
17. O. Yodsaoue, J. Sonprasit, C. Karalai, C. Ponglimanont, S. Tewtrakul, and S. Chantrapromma Phytochemistry 76 2012 83 91
18. Y.-J. Xu, X.-H. Wu, B.K.H. Tan, Y.-H. Lai, J.J. Vittal, Z. Imiyabir, L. Madani, K.S. Khozirah, and S.H. Goh J. Nat. Prod. 63 2000 473 476
19. K. Chiba, T. Hirano, Y. Kitano, and M. Tada Chem. Commun. 1999 691 692
20. J. Barluenga, M. Trincado, E. Rubio, and J.M. González J. Am. Chem. Soc. 126 2004 3416 3417
21. Y. Yamamoto, and K. Itonaga Org. Lett. 11 2009 717 720
22. T.T. Dang, F. Boeck, and L. Hintermann J. Org. Chem. 76 2011 9353 9361
23. H. Hamamoto, K. Hata, H. Nambu, Y. Shiozaki, H. Tohma, and Y. Kita Tetrahedron Lett. 45 2004 2293 2295
24. H. Sugimoto, S. Nakamura, and T. Ohwada Adv. Synth. Catal. 349 2007 669 679
25. B.M. Trost, H.C. Shen, L. Dong, J.-P. Surivet, and C. Sylvain J. Am. Chem. Soc. 126 2004 11966 11983
26. E.A. Couladouros, V.I. Moutsos, M. Lampropoulou, J.L. Little, and J.A. Hyatt J. Org. Chem. 72 2007 6735 6741
27. E.S. Mull, M.V. Zandt, A. Golebiowski, R.P. Beckett, P.K. Sharma, and H. Schroeter Tetrahedron Lett. 53 2012 1501 1503
28. For a recent review on the asymmetric synthesis of chromans, see: H.C. Shen Tetrahedron 65 2009 3931 3952
29. K.-I. Oyama, and T. Kondo J. Org. Chem. 69 2004 5240 5246
30. Y. Li, J. Yang, W.Z. Li, L. Hou, J. Xue, and Y. Li J. Nat. Prod. 64 2001 214 216
31. K. Li, K. Vanka, W.H. Thompson, and J.A. Tunge Org. Lett. 8 2006 4711 4714
32. K.J. Hodgetts Tetrahedron 61 2005 6860 6870
33. L. Zhang, W.-G. Zhang, E.-L. Ma, L. Wu, K. Bao, X.-L. Wang, Y.-L. Wang, and H.-R. Song Arch. Pharm. Chem. Life Sci. 340 2007 650 655
34. O. Mazimba, I.B. Masesane, and R.R. Majinda Tetrahedron Lett. 52 2011 6716 6718
35. B. Nay, M. Collet, M. Lebon, C. Chèze, and J. Vercauteren Tetrahedron Lett. 43 2002 2675 2678
36. S. Radomkit, P. Sarnpitak, J. Tummatorn, P. Batsomboon, S. Ruchirawat, and P. Ploypradith Tetrahedron 67 2011 3904 3914
37. A.H.L. Machado, M.A.D. Sousa, D.C.S. Patto, L.F.S. Azevedo, F.I. Bombonato, and C.R.D. Correia Tetrahedron Lett. 50 2009 1222 1225
38. T. Tatsuta, T. Tamura, and T. Mase Tetrahedron Lett. 40 1999 1925 1928
39. S.B. Bharate, R. Mudududdla, J.B. Bharate, N. Battini, S. Battula, R.R. Yadav, B. Singhb, and R.A. Vishwakarma Org. Biomol. Chem. 10 2012 5143 5150
40. V.K. Ahluwalia, K.K. Arora, and K. Mukherjee Synthesis 1984 346 348
41. D.G. Roux, and G.C. Debruyn Biochem. J. 87 1963 435 439
42. C. Selenski, and T.R.R. Pettus Tetrahedron 62 2006 5298 5307
43. M. Palucki, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 10333 10334
44. K.E. Torraca, S.-i. Kuwabe, and S.L. Buchwald J. Am. Chem. Soc. 122 2000 12907 12908
45. S.-i. Kuwabe, K.E. Torraca, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 12202 12206
46. Q. Shelby, N. Kataoka, G. Mann, and J. Hartwig J. Am. Chem. Soc. 122 2000 10718 10719
47. N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553 5566
48. A. Neogi, T.P. Majhi, B. Achari, and P. Chattopadhyay Eur. J. Org. Chem. 2 2008 330 336
49. X. Wu, B.P. Fors, and S.L. Buchwald Angew. Chem., Int. Ed. 50 2011 9943 9947
50. Angew. Chem. 123 2011 10117 10121
51. X.B. Jing, C.G. Yan, J. Sun, L. Wang, and L. An Chin. Chem. Lett. 15 2004 1392 1394
52. S. Gowrisankar, A.G. Sergeev, P. Anbarasan, A. Spannenberg, H. Neumann, and M. Beller J. Am. Chem. Soc. 132 2010 11592 11598
53. J. Niu, P. Guo, J. Kang, Z. Li, J. Xu, and S. Hu J. Org. Chem. 74 2009 5075 5078
54. H. Adams, N.J. Gilmore, S. Jones, M.P. Muldowney, S.H. von Reuss, and R. Vemula Org. Lett. 10 2008 1457 1460
55. Y. Fang, and C. Li J. Org. Chem. 71 2006 6427 6431
56. Y. Wang, and R. Franzén Synlett 2012 925 929
57. G.S. Kumar, C.U. Maheswari, R.A. Kumar, M.L. Kantam, and K.R. Reddy Angew. Chem., Int. Ed. 50 2011 11748 11751
58. Angew. Chem. 123 2011 11952 11955
59. A.G.K. Reddy, J. Krishna, and G. Satyanarayana Synlett 2011 1756 1760
60. J. Krishna, A.G.K. Reddy, L. Mahendar, and B.V. Ramulu Synlett 2012 375 380
61. L. Mahendar, J. Krishna, A.G.K. Reddy, and B.V. Ramulu Org. Lett. 14 2012 628 631
62. A.G.K. Reddy, and G. Satyanarayana Tetrahedron 68 2012 8003 8010
63. B. Suchand, J. Krishna, B.V. Ramulu, D. Dibyendu, A.G.K. Reddy, L. Mahendar, and G. Satyanarayana Tetrahedron Lett. 53 2012 3861 3864
64. A.G.K. Reddy, J. Krishna, and G. Satyanarayana Tetrahedron Lett. 53 2012 5635 5640
65. J. Krishna, A.G.K. Reddy, and G. Satyanarayana Synlett 2013 967 972
66. T. Jeffery Tetrahedron Lett. 32 1991 2121 2124
67. T. Jeffery Tetrahedron Lett. 31 1990 6641 6644
68. J. Muzart Tetrahedron 59 2003 5789 5816
69. J. Muzart Tetrahedron 61 2005 4179 4212
70. J. Muzart Tetrahedron 59 2005 5955 6008
71. For the relevant examples of [Pd]-catalyzed coupling of iodobenzenes with aryl vinyl alcohols, see: A. Briot, C. Baehr, R. Brouillard, A. Wagner, and C. Mioskowski J. Org. Chem. 69 2004 1374 1377
72. L.F. Tietze, K. Kahle, and T. Raschke Chem. - Eur. J. 8 2002 401 407
73. D. Bruyére, D. Bouyssi, and G. Balme Tetrahedron 60 2004 4007 4017
74. G. Satyanarayana, and M.E. Maier Tetrahedron 64 2008 356 363
75. G. Satyanarayana, and M.E. Maier J. Org. Chem. 73 2008 5410 5415
76. G. Satyanarayana, and M.E. Maier Org. Lett. 10 2008 2361 2364
77. G. Satyanarayana, C. Maichle-Mössmer, and M.E. Maier Chem. Commun. 2009 1571 1573