Regiospecific synthesis of arenofurans via cascade reactions of arenols with Morita-Baylis-Hillman acetates of nitroalkenes and total synthesis of isoparvifuran

Tetrahedron

Volumn 69, Issue 24, 2013, Pages 4964-4972

  Kumar, Tarun ^a   Mobin, Shaikh M ^b   Namboothiri, Irishi N N ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY INDORE   (India)

Author keywords

Arenofurans; Cascade reaction; Isoparvifuran; Morita Baylis Hillman acetates; Nitroalkenes

Indexed keywords

1 NAPHTHOL; 2 NAPHTHOL; ACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; ANTIFUNGAL AGENT; ARENOFURAN DERIVATIVE; FURAN DERIVATIVE; ISOPARVIFURAN; MORITA BAYLIS HILLMAN ACETATE; NITROALKENE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; METHODOLOGY; MICHAEL ADDITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84877584892     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.023     Document Type: Article

References (89)

1. B.A. Keay, and P.W. Dibble Comprehensive Heterocyclic Chemistry II Vol. 2 1997 Elsevier Oxford, UK 395
2. D.M.X. Donnelly, and M.J. Meegan A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry II Vol. 4 1984 Pergamon Oxford, UK 657 Selected reviews
3. R.C.D. Brown Angew. Chem., Int. Ed. 44 2005 850
4. X.L. Hou, H.Y. Cheung, T.Y. Hon, P.L. Kwan, T.H. Lo, S.Y. Tong, and H.N.C. Wong Tetrahedron 54 1998 1955
5. S.F. Kirsch Org. Biomol. Chem. 4 2006 2076
6. R.R. Rao, V. Chaturvedi, K.S. Babu, P.P. Reddy, V.R.S. Rao, P. Sreekanth, A.S. Sreedhar, and J.M. Rao Med. Chem. Res. 21 2012 634 Tubulin polymerization inhibitor
7. D.J. Kerr, E. Hamel, M.K. Jung, and B.L. Flynn Bioorg. Med. Chem. 15 2007 3290 Anti-microbial
8. M.W. Khan, M.J. Alam, M.A. Rashid, and R. Chowdhury Bioorg. Med. Chem. 13 2005 4796
9. N. Zanatta, S.H. Alves, H.S. Coelho, D.M. Borchhardt, P. Machado, K.M. Flores, F.M. Silva, T.B. Spader, J.M. Santurio, H.G. Bonacorso, and M.A.P. Martins Bioorg. Med. Chem. 15 2007 1947
10. C. Paal Chem. Ber. 18 1885 367
11. L. Knorr Chem. Ber. 18 1885 299
12. J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, and W. Su Tetrahedron Lett. 47 2006 5383
13. G. Ravindran, S. Muthusubramanian, S. Selvaraj, and S. Perumal ARKIVOC 2007 23
14. G. Minetto, L.F. Raveglia, A. Sega, and M. Taddei Eur. J. Org. Chem. 2005 5277
15. I. Yavari, M.A. Abbasinejad, and A. Alizadeh Tetrahedron Lett. 43 2002 4503
16. F. Feist Chem. Ber. 35 1902 1537
17. E. Benary Chem. Ber. 44 1911 489
18. G. Mross, E. Holtz, and P. Langer J. Org. Chem. 71 2006 8045
19. N. Ayyagari, D. Jose, S.M. Mobin, and I.N.N. Namboothiri Tetrahedron Lett. 52 2011 258
20. A.S.K. Hashmi, L. Schwarz, J.-H. Choi, and T.M. Frost Angew. Chem., Int. Ed. 39 2000 2285
21. S. Ma, J. Zhang, and L. Lu Chem. - Eur. J. 9 2003 2447
22. J.A. Marshall, and G.S. Bartley J. Org. Chem. 59 1994 7169
23. A.S. Dudnik, and V. Gevorgyan Angew. Chem., Int. Ed. 46 2007 5195
24. J.M. Aurrecoechea, A. Durana, and E. Perez J. Org. Chem. 73 2008 3650
25. A.S.K. Hashmi, T. Haeffner, M. Rudolph, and F. Rominger Eur. J. Org. Chem. 4 2011 667
26. A.S.K. Hashmi Angew. Chem., Int. Ed. 34 1995 1581
27. A.S.K. Hashmi, T.L. Ruppert, T. Knöfel, and J.W. Bats J. Org. Chem. 62 1997 7295
28. Fluorescent probe: M.A. Aziz, J.V. Auping, and M.A. Meador J. Org. Chem. 60 1995 1303
29. Photosensitizer: P.K. Frederiksen, M. Jorgensen, and P.R. Ogilby J. Am. Chem. Soc. 123 2001 1215
30. M.E. Garst, and T.A. Spencer J. Am. Chem. Soc. 95 1973 250
31. M.E. Garst, and T.A. Spencer J. Org. Chem. 48 1983 2442
32. Z.Z. Song, M.S. Ho, and H.N.C. Wong J. Org. Chem. 59 1994 3917
33. M. Kurosu, L.R. Marcin, and Y. Kishi Tetrahedron Lett. 39 1998 8929
34. A.R. Katritzky, D. Hür, K. Kirichenko, Y. Ji, and P.J. Steel ARKIVOC 2004 109
35. M. Kurosu, and Y. Kishi J. Synth. Org. Chem., Jpn. 2004 1205
36. R.L. Danheiser, and S.K. Gee J. Org. Chem. 49 1984 1672
37. J.O. Karlsson, N.V. Nguyen, L.D. Foland, and H.W. Moore J. Am. Chem. Soc. 107 1985 3392
38. D.C. Harrowven, D.D. Pascoe, and I.L. Guy Angew. Chem., Int. Ed. 46 2007 425
39. X.Y. Mak, A.L. Crombie, and R.L. Danheiser J. Org. Chem. 76 2011 1852
40. J. Nickl Chem. Ber. 91 1958 553
41. L. Bolzoni, G. Casiraghi, G. Casnati, and G. Sartori Angew. Chem., Int. Ed. 17 1978 684
42. H.D. Choi, P.J. Seo, B.W. Son, and B.W. Kang Arch. Pharm. Res. 27 2004 19
43. Y. Liang, L.M. Tao, Y.H. Zhang, and J.H. Li Synthesis 2008 3988
44. A.K. Yadav, B.K. Singh, N. Singh, and R.P. Tripathi Tetrahedron Lett. 48 2007 6628
45. W.H. Perkin J. Chem. Soc. 20 1867 568
46. W.H. Perkin J. Chem. Soc. 24 1871 37
47. K. Bowden, and S. Battah J. Chem. Soc., Perkin Trans. 2 1998 1603
48. Review: I.R. Johnson Org. React. 1 1942 210
49. E. Rapp Gazz. Chim. Ital. 25 1895 285
50. R. Stoermer Justus Liebigs Ann. Chem. 312 1900 237
51. M.L.N. Rao, D.K. Awasthi, and D. Banerjee Tetrahedron Lett. 48 2007 431
52. L. De Luca, G. Nieddu, A. Porcheddu, and G. Giacomelli Curr. Med. Chem. 16 2009 1
53. Z. Wang, J. Gu, H. Jing, and Y. Liang Synth. Commun. 39 2009 4079
54. A. Hassner, and I. Namboothiri Organic Syntheses Based on Name Reactions 3rd ed. A Practical Guide to 750 Transformations 2012 Elsevier Oxford, UK
55. G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285 Selected articles, oxidative cyclization
56. S.W. Youn, and J.I. Eom Org. Lett. 6 2005 3355
57. T. Satoh, T. Tsuda, Y. Kushino, M. Miura, and M. Nomura J. Org. Chem. 61 1996 6476 Via propargylation of indoles and phenols
58. Z. Liu, L. Lui, Z. Shafiq, Y.C. Wu, D. Wang, and Y.J. Chen Synthesis 13 2007 1961 Via RCM
59. W.A.L. van Otterlo, G.L. Morgans, L.G. Madeley, S. Kuzvidza, S.S. Moleele, N. Thornton, and C.B. de Koning Tetrahedron 61 2005 7746 Via intramolecular Heck reaction
60. X. Xie, B. Chen, J. Lu, J. Han, X. She, and X. Pan Tetrahedron Lett. 45 2004 6235 From 3-silyloxy-1,5-enynes
61. A.S.K. Hashmi, W. Yang, and F. Rominger Angew. Chem., Int. Ed. 50 2011 5762
62. A.S.K. Hashmi, W. Yang, and F. Rominger Chem. - Eur. J. 18 2012 6576
63. Via cyclofragmentation: K.C. Nicolaou, S.A. Snyder, A. Bigot, and J.A. Pfefferkorn Angew. Chem., Int. Ed. 39 2000 1093
64. From α-hydroxyphenyl ketones: A.R. Katritzky, Y. Ji, Y. Fang, and I. Prakash J. Org. Chem. 66 2001 5613
65. From naphthol/phenol and α-haloketone: M. Jorgensen, F.C. Krebs, and K. Bechgaard J. Org. Chem. 65 2000 8783
66. J. Habermann, S.V. Ley, and R. Smits J. Chem. Soc., Perkin Trans. 1 1999 2421
67. From N-(phenoxymethyl)-benzotriazoles: A.R. Katritzky, L. Serdyuk, and L. Xie J. Chem. Soc., Perkin Trans. 1 1998 1059
68. From o-alkoxybenzoylarene derivatives: G.A. Kraus, N. Zhang, J.G. Verkade, M. Nagarajan, and P.B. Kisanga Org. Lett. 2 2000 2409
69. K.K. Park, and J. Jeong Tetrahedron 61 2005 545
70. G.A. Kraus, and J.D. Schroeder Synlett 2005 2504
71. From captodative olefins: M.C. Cruz, and J. Tamariz Tetrahedron Lett. 45 2004 2377
72. Via intramolecular photocyclization: K.K. Park, H. Seo, J.G. Kim, and I.H. Suh Tetrahedron Lett. 41 2000 1393
73. I. Deb, M. Dadwal, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 8 2006 1201
74. I. Deb, P. Shanbhag, S.M. Mobin, and I.N.N. Namboothiri Eur. J. Org. Chem. 2009 4091
75. Furans and pyrans: D.K. Nair, S.M. Mobin, and I.N.N. Namboothiri Tetrahedron Lett. 53 2012 3349
76. Imidazopyridines: D.K. Nair, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 14 2012 4580
77. Furans and pyrans: W.Y. Huang, Y.C. Chen, and K. Chen Chem. - Asian J. 7 2012 688
78. Cyclopentenes: L.F. Yeh, S. Anwar, and K. Chen Tetrahedron 68 2012 7317
79. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jpn. 41 1968 2815
80. Baylis, A. B.; Hillman, M. E. D. Ger. Offen. 1972, DE 2155113. Selected recent reviews
81. D. Basavaiah, and G. Veeraraghavaiah Chem. Soc. Rev. 41 2012 68
82. M. Shi, F. Wang, M.X. Zhao, and Y. Wei The Chemistry of the Morita-Baylis-Hillman Reaction 2011 Royal Society of Chemistry
83. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1
84. V. Singh, and S. Batra Tetrahedron 64 2008 4511
85. K. Kaur, and I.N.N. Namboothiri Chimia 66 2012 913
86. N. Muangnoicharoen, and A.W. Frahm Phytochemistry 20 1981 291
87. D.M.X. Donnelly, T.O. Criodain, and M.J.C.S. O'Sollivan J. Chem. Soc., Chem. Commun. 1981 1254 Partial synthesis
88. S. Walia, S.K. Kulshrestha, and S.K. Mukerjee Tetrahedron 42 1986 4817
89. 3 in DCM has appeared: S. Anwar, W.-Y. Huang, C.-H. Chen, Y.-S. Cheng, and K. Chen Chem. - Eur. J. 19 2013 4344