Studies on the Michael addition of naphthoquinones to sugar nitro olefins: First synthesis of polyhydroxylated hexahydro-11H-benzo[a]carbazole-5,6-diones and hexahydro-11bH-benzo[b]carbazole-6,11-diones

Tetrahedron

Volumn 68, Issue 5, 2012, Pages 1612-1621

  Otero, José M ^a,b   Barcia, José C ^a,b   Salas, Cristian O ^c   Thomas, Pablo ^c   Estévez, Juan C ^a,b   Estévez, Ramón J ^a,b  

^a s n   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Henry reaction; Indoles; Michael addition; Nitro compounds; Quinones; Sugar

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; CARBAZOLE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; GLUCOSE; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; NAPHTHOXAZINE DERIVATIVE; NITRO DERIVATIVE; SUGAR;

ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; HYDROXYLATION; MICHAEL ADDITION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 84855583227     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.072     Document Type: Article

References (65)

1. S. Patai, and Z. Rappoport The Chemistry of Functional Groups: The Chemistry of the Quinonoid Compounds 1988 Wiley New York, NY
2. P.J. O'Brien Chem. Biol. Interact. 80 1991 1
3. R.H. Thomson Naturally Occurring Quinones 4th ed. 1997 Chapman and Hall London/New York, NY
4. J.A. Duke CRC Handbook of Medicinal Herbs 1985 CRC Boca Raton p 470
5. S. Spyroudis Molecules 5 2000 1291
6. A. Ravelo, A. Estévez-Braun, H. Chávez-Orellana, E. Pérez-Sacau, and D. Mesa-Silverio Curr. Top. Med. Chem. 4 2004 241
7. C.R. Solorio-Alvarado, E. Peña-Cabrera, J. García-Solto, J. López-Godínez, F.J. González, and A. Alvarez- Hernández Arkivoc 2009 239
8. F. Karci, and N. Ertan Color. Technol. 121 2005 153
9. D.K. Barange, V. Kavala, B.R. Raju, C.-W. Kuo, C. Tseng, Y.-C. Tu, and C.-F. Yao Tetrahedron Lett. 50 2009 5116 and references cited therein
10. E.P. Sacau, A. Estévez-Braun, A.G. Ravelo, E.A. Ferro, H. Tokuda, T. Mukainakac, and H. Nishino Bioorg. Med. Chem. 11 2003 483
11. A. Baramee, A. Coppin, M. Mortuaire, L. Pelinski, S. Tomavoc, and J. Brocard Bioorg. Med. Chem. 14 2006 1294
12. K. Eyong, P.S. Kumar, V. Kuete, G.N. Folefoc, E.A. Nkengfack, and S. Baskaran Bioorg. Med. Chem. Lett. 18 2008 5387 and references cited therein
13. J.P.A. Harrity, W.J. Kerr, D. Middlemiss, and J.S. Scott J. Organomet. Chem. 532 1997 219 and references cited therein
14. J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 34 1993 6479
15. Y.-L. Luo, T.-C. Chou, and C.C. Cheng J. Heterocycl. Chem. 33 1996 113
16. H.-J. Knölker, and K.R. Reddy Chem. Rev. 102 2002 4303
17. J. Cruces, J.C. Estévez, L. Castedo, and R.J. Estévez Tetrahedron Lett. 42 2001 4825
18. J. Cruces, E. Martínez, M. Treus, L.A. Martínez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron 58 2002 3015
19. J.C. Barcia, J. Cruces, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 43 2002 5141
20. M. Fernández, C. Barcia, J.C. Estévez, R.J. Estévez, and L. Castedo Synlett 2004 267
21. C. Asche, W. Frank, A. Albert, and U. Kucklaender Bioorg. Med. Chem. 13 2005 819
22. P.H. Bernando, C.L.L. Chai, M. Le Guen, G.D. Smith, and P. Waring Bioorg. Med. Chem. Lett. 17 2007 82
23. Q.A. Khan, J. Lu, and S.M. Hecht J. Nat. Prod. 72 2009 438
24. C.C. Ceng G.P. Ellis, G.B. West, Progress in Medicinal Chemistry, Structural Aspects of Antineoplastic Agents - A New Approach Vol. 25 1988 Elsevier Amsterdam
25. C. Rehn, and U. Pindur Monatsh. Chem. 127 1996 645
26. G.R. Pettit, V. Gaddamidi, and G.M. Cragg J. Nat. Prod. 47 1984 1018
27. B. Gabrielsen, T.P. Monath, J.W. Huggins, J.J. Kirsi, M. Hollingshead, W.M. Shannon, and G.R. Pettit C.K. Chu, H.G. Cutler, Natural Products as Antiviral Agents 1992 Plenum New York, NY pp 121-135
28. R.M. Patel, and R.N. Prajapati Biotechnol. Mol. Biol. Rev. 6 2011 59
29. L. Henry C. R. Acad. Sci. Paris 120 1895 1265
30. O. Noboru The Nitro Group in Organic Synthesis H. Feuer, Organic Nitro Chemistry Series 2001 Wiley-VCH Chapter 2
31. F.A. Luzzio Tetrahedron 57 2001 915
32. J. Boruwa, N. Gogoi, P.P. Saikia, and N.C. Barua Tetrahedron: Asymm. 17 2006 3315
33. C. Palomo, M. Oiarbide, and A. Laso Eur. J. Org. Chem. 2007 2561
34. R.G. Soengas, J.C. Estévez, A.M. Estévez, F. Fernández, and R.J. Estévez Carbohydr. Chem. 35 2009 173
35. R.G. Soengas, J.C. Estévez, R.J. Estévez, and M.A. Maestro Tetrahedron: Asymm. 14 2003 1653 and references cited therein
36. R. Soengas, J.C. Estévez, and R.J. Estévez Org. Lett. 5 2003 4457
37. C. Chakraborty, V.P. Vyavahare, V.G. Puranik, and D.D. Dhavale Tetrahedron 64 2008 9574
38. C.J. O'Connor, M.D. Roydhouse, A.M. Przybyl, M.D. Wall, and J.M. Sothern J. Org. Chem. 75 2010 2534
39. To the best of our knowledge, the first reported Michael addition of 2-hydroxy-1,4-naphthoquinone to a nitro olefin was: J.C. Barcia, J.M. Otero, J.C. Estévez, and R.J. Estévez Synlett 2007 1399
40. For further Michael addition of 2-hydroxy-1,4-naphthoquinone to nitro olefins, see: M. Yu, H.C. Malinakove, and K.W. Stagliano J. Org. Chem. 71 2006 6648
41. W.-M. Zhou, H. Liu, and D.-M. Du Org. Lett. 10 2008 2817
42. J.M. Otero, F. Fernández, J.C. Estévez, and R.J. Estévez Tetrahedron: Asymm. 16 2005 4045
43. Nitrocyclohexene was prepared according to: E.J. Corey, and H. Estreicher J. Am. Chem. Soc. 100 1978 6294
44. K. Kobayasi, T. Taki, M. Kawakita, M. Uchida, O. Morikawa, and H. Konishi Heterocycles 51 1999 349
45. For previous similar cyclizations leading to oxygen heterocycles, see: Y.R. Lee, K.Y. Kang, G.J. Lee, and W.K. Lee Synthesis 2003 1977
46. Y.R. Lee, and B.S. Kim Synth. Commun. 33 2003 4123
47. W. Nair, P.M. Treesa, D. Maliakal, and N.P. Rath Tetrahedron 57 2001 7705
48. For recent publications, see: R.G. Soengas, J.C. Estévez, and R.J. Estévez Tetrahedron 59 2003 6285
49. R. Soengas, J.C. Estévez, and R.J. Estévez Org. Lett. 5 2003 1423
50. R.G. Soengas, M.B. Pampín, J.C. Estévez, and R.J. Estévez Tetrahedron: Asymm. 16 2005 205
51. J.M. Otero, R. Soengas, J.C. Estévez, R.J. Estévez, D.J. Watkin, E.L. Evinson, R.J. Nash, and G.W. Fleet J. Org. Lett. 9 2007 623
52. J.M. Otero, A.M. Estévez, R.G. Soengas, J.C. Estévez, R.J. Nash, G.W.J. Fleet, and R.J. Estévez Tetrahedron: Asymm. 19 2008 2443
53. A.M. Estévez, R.G. Soengas, J.M. Otero, J.C. Estévez, R.J. Nash, and R.J. Estévez Tetrahedron: Asymm. 21 2010 21
54. J. Kovar, and H.H. Baer Can. J. Chem. 51 1973 1801
55. J. Kovar, and H.H. Baer Carbohydr. Res. 39 1975 19
56. R. Ballini, and C. Palestini Tetrahedron Lett. 35 1994 5731
57. G.W.J. Fleet, and P.W. Smith Tetrahedron 43 1987 971
58. M. Funabashi, K. Kobayashi, and J. Yoshimura J. Org. Chem. 44 1979 1618
59. The crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as deposition number CCDC 823584 (17) and CCDC 254541 (21a-2). Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk ].
60. M. Chérest, H. Felkin, and N. Prudent Tetrahedron Lett. 9 1968 2199
61. R.F. Hoffmann Chem. Rev. 89 1989 1841
62. P.A. Evans, and T.A. Brandt J. Org. Chem. 62 1997 5321
63. J. Bloomer, and W. Zheng Synth. Commun. 28 1998 2087
64. This chelation effect of lithium-nucleophiles was reported previously by other authors: R.F.W. Jackson, N.J. Palmer, M.J. Wythes, W. Clegg, and M.R.J. Elsegood J. Org. Chem. 60 1995 6431
65. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 1988 Pergamon New York NY