Radical cyclization of ynamides into six- or eight-membered rings. Application to the synthesis of a protoberberine analog

Tetrahedron Letters

Volumn 52, Issue 22, 2011, Pages 2876-2880

  Balieu, Sébastien ^a   Toutah, Krimo ^a   Carro, Laura ^a   Chamoreau, Lise Marie ^b   Rousselière, Hélène ^b   Courillon, Christine ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Alkaloids; Cyclization; Nitrogen heterocycles; Radicals; Ynamides

Indexed keywords

MANITIMUS; PROTOBERBERINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION;

EID: 79955568058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.118     Document Type: Article

References (60)

1. C.A. Zificsak, J.A. Mulder, R.P. Hsung, C. Rameshkumar, and L. Wei Tetrahedron 57 2001 7575 7606
2. F. Marion, C. Courillon, and M. Malacria Org. Lett. 5 2003 5095 5097
3. F. Marion, J. Coulomb, A. Servais, C. Courillon, L. Fensterbank, and M. Malacria Tetrahedron 62 2006 3856 3871
4. K.A. DeKorver, H. Li, A.G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, and R.P. Hsung Chem. Rev. 110 2010 5064 5106
5. A. Sato, H. Yorimitsu, and K. Oshima Bull. Korean Chem. Soc. 31 2010 570 576
6. E. Reimann Curr. Org. Chem. 4 2009 353 378 and references cited therein
7. T. Kameni, N. Takagi, M. Toyota, T. Honda, and K. Fukumoto Heterocycles 16 1981 591 602
8. A.I. Meyers, M. Boes, and D.A. Dickman Angew. Chem., Int. Ed. 23 1984 458 462
9. M.J. Munchhof, and A.I. Meyers J. Org. Chem. 61 1996 4607 4610
10. L. Carillo, D. Badia, E. Dominguez, E. Anakabe, I. Orsante, I. Tellitu, and J.L. Vicario J. Org. Chem. 64 1999 1115 1118
11. T.N. Le, S.G. Gang, and W.J. Chao J. Org. Chem. 69 2003 2768 2772
12. A. Navarro-Vázquez, D. Rodríguez, M.F. Martínez- Esperón, A. García, C. Saá, and D. Domínguez Tetrahedron Lett. 48 2007 2741 2743
13. T. Fukuda, and M. Iwao Heterocycles 74 2007 701 720
14. J.K. Chang, and N.C. Chang Tetrahedron 64 2008 3483 3487
15. P.B. Wakchaure, S. Easwar, and N. Argade Synthesis 10 2009 1667 1672
16. C.S. Lee, T.C. Yu, J.W. Luo, Y.Y. Cheng, and C.P. Chuang Tetrahedron Lett. 50 2009 4558 4562
17. G.E. Lee, H.S. Lee, S.D. Lee, J.H. Kim, W.K. Kim, and Y.C. Kim Bioorg. Med. Chem. Lett. 19 2009 954 958
18. M. Klimek, and L. Hnilica Arch. Biochem. Biophys. 81 1959 105 110
19. M. Yamagishi J. Cell Biol. 15 1962 589 592
20. A.K. Krey, and F.E. Hahn Science 166 1969 755 757
21. M.W. Davidson, I. Loop, S. Alexander, and W.D. Wilson Nucleic Acids Res. 4 1977 2697 2712
22. M. Cushman, F.W. Dekow, and L.B. Jacobsen J. Med. Chem. 22 1979 331 333
23. A. Rungsitiyakorn, P. Wilairat, and B. Panjipan J. Pharm. Pharmacol. 33 1981 125 127
24. W.H. Chen, Y. Qin, Z. Cai, C.L. Chan, G.A. Luo, and Z.H. Jiang Bioorg. Med. Chem. 13 2005 1859 1866
25. M. Maiti, and G.S. Kumar Med. Res. Rev. 5 2007 649 695
26. L. Grycová, J. Dostál, and R. Marek Phytochemistry 68 2007 150 175
27. R. Sinsha, and G.S. Kumar J. Phys. Chem. B 113 2009 13410 13420
28. F.A. Davis, and P.K. Mohanty J. Org. Chem. 67 2002 1290 1296 and references cited therein
29. Z. Janousek, J. Collard, and H.G. Viehe Angew. Chem., Int. Ed. Engl. 11 1972 917 918
30. H.E. Zaug, L.R. Swett, and G.R. Stone J. Org. Chem. 23 1958 1389 1390
31. R.P. Hsung, C.A. Zificsak, L.-L. Wie, C.J. Douglas, J.A. Mulder, and H. Xiong Org. Lett. 1 1999 1237 1240
32. A. Balsamo, B. Macchia, F. Macchia, and A. Rosselo Tetrahedron Lett. 26 1985 4141 4144
33. J.R. Dunetz, and R.L. Danheiser Org. Lett. 5 2003 4011 4014
34. B. Witulski, and T. Stengel Angew. Chem., Int. Ed. 37 1998 489 492
35. M. Mori, K. Chiba, and Y. Ban J. Org. Chem. 1978 1684 1687
36. J.N. Johnston, M.A. Plotkin, R. Viswanathan, and E.N. Prabhakaran Org. Lett. 3 2001 1009 1011
37. R. Viswanathan, E.N. Prabhakaran, M.A. Plotkin, and J.N. Johnston J. Am. Chem. Soc. 125 2003 163 168
38. M. Soledad, C. Pedras, A.Q. Kahn, K.C. Smith, and S.L. Stettner Can. J. Chem. 75 1997 825 828
39. N. Zefirov, V. Zhdankin, and A. Koz'min Izvestiya Akad. Nauk SSSR, Seriya Khim. 7 1983 1530 1531
40. General procedure for the formation of ynamides: KHMDS (5.36 mL, 2.68 mmol, 0.5 M solution in toluene) was added to a solution of amide (2.42 mmol) in anhydrous toluene (90 mL) at room temperature. The reaction mixture was heated to 80 °C for 2 h. Phenyl-trimethylsilyl ethynyl iodonium triflate (3.03 mmol) was then added. After 30 min the resulting mixture was cooled to room temperature, quenched with 12 g of silica, then concentrated and the residue was purified by flash chromatography (petroleum ether/diethylether 90:10).
41. C.R. Hauser, and M.J. Weiss J. Org. Chem. 14 1949 310 321
42. G.R. Newkome, Y.J. Joo, D.W. Evans, S. Pappalardo, and F.R. Fronczek J. Org. Chem. 53 1988 786 790
43. General procedure for radical cyclization: Tributyltin hydride (0.88 mmol) and AIBN (0.22 mmol) were added to a degassed solution of ynamide (0.44 mmol) in benzene (30 mL). The reaction mixture was refluxed until TLC indicated that the starting material had completely reacted, then cooled to room temperature. 1 M aq NaOH (30 mL) was added and the resulting mixture was stirred for 30 min then extracted with ethyl acetate (2 × 40 mL), dried over MgSO4 and concentrated. The residue was purified by flash chromatography (petroleum ether/ethyl acetate: 97:3) to afford the cyclized products.
44. A. Hallberg, A. Svensson, and A.R. Martin Tetrahedron Lett. 27 1986 1959 1962
45. Z. Liu, and R.C. Larock J. Am. Chem. Soc. 127 2005 13112 13113
46. 3: calcd 264.0612; found 264.0616, CCDC 772462 contains the supplementary crystallographic data for this molecule.
47. 3Na: calcd 330.1106; found 330.1103. CCDC 772463 contains the supplementary crystallographic data for this molecule.
48. C. Anies, J.-Y. Lallemand, and A. Pancrazi Tetrahedron Lett. 37 1996 5523 5526
49. A.M. Gómez, E. Moreno, S. Valverde, and J.C. López Chem. Commun. 1999 175 176
50. A.M. Gómez, E. Moreno, S. Valverde, and J.C. López Tetrahedron Lett. 43 2002 5559 5562
51. A.M. Gómez, E. Moreno, S. Valverde, and J.C. López Tetrahedron Lett. 43 2002 7863 7866
52. I.V. Alabugin, K. Gilmore, S. Patil, M. Manoharan, S.V. Kovalenko, R.J. Clark, and I. Ghiviriga J. Am. Chem. Soc. 130 2008 11535 11545
53. Y.-L. Kuo, M. Dhanasekaran, and C.-K. Sha J. Org. Chem. 74 2009 2033 2038
54. S.B. Jones, B. Simmons, and D.W.C. MacMillan J. Am. Chem. Soc. 131 2009 13606 13607
55. 3NaSi: calcd 350.1164; found 350.1167. CCDC 772464 contains the supplementary crystallographic data for this molecule.
56. C.U. Dinesh, and H.-U. Reissig Angew. Chem., Int. Ed. 38 1999 789 791
57. E. Nandanan, C.U. Dinesh, and H.-U. Reissig Tetrahedron 56 2000 4267 4277
58. S.N. Joshi, U.D. Phalgune, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron Lett. 44 2003 1827 1830
59. C. Ferrer, C.H.M. Amijs, and A.M. Echavarren Chem. Eur. J. 13 2007 1358 1373
60. C. Ferrer, A. Escribano-Cuesta, and A.M. Echavarren Tetrahedron 65 2009 9015 9020