Synthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closure

Tetrahedron

Volumn 61, Issue 5, 2005, Pages 1155-1165

  Sarkar, Tarun K ^a   Hazra, Anindya ^a   Gangopadhyay, Pulak ^a   Panda, Niranjan ^a   Slanina, Zdenek ^b   Lin, Chun Cheng ^c   Chen, Hui Ting ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Aza ene reaction; Fused tetrahydropyrazole; Heterocyclic allylsilanes; Macronecine; Necine bases; Supinidine

Indexed keywords

PYRROLIZIDINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THEORETICAL STUDY;

EID: 12344250842     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.046     Document Type: Article

References (64)

1. For reviews see: (a) X.L.M. Despinoy, and H. McNab Tetrahedron 56 2000 6359
2. J.R. Liddell Nat. Prod. Rep. 16 1999 499
3. G. Casiraghi, F. Zanardi, G. Rassu, and L. Pinna Org. Prep. Proc. Int. 28 1996 643
4. J.R. Liddell Nat. Prod. Rep. 13 1996 187
5. D.J. Robins Nat. Prod. Rep. 12 1995 413
6. D.J. Robins Nat. Prod. Rep. 9 1992 313
7. E. Langkopf, and D. Schinzer Chem. Rev. 95 1995 1375
8. H. Hiemstra, M.H.A.M. Sno, R.J. Vijn, and W.N. Speckamp J. Org. Chem. 50 1985 4014
9. H. Hiemstra, and W.N. Speckamp Tetrahedron Lett. 24 1983 1407
10. T.K. Sarkar, S.K. Ghosh, P.S.V. Subba Rao, and T.K. Satapathi Tetrahedron Lett. 31 1990 3461
11. T.K. Sarkar, B.K. Ghorai, S.K. Nandy, and B. Mukherjee Tetrahedron Lett. 35 1994 6903
12. T.K. Sarkar, S.K. Ghosh, P.S.V. Subba Rao, and V.R. Mamdapur Tetrahedron Lett. 31 1990 3456
13. T.K. Sarkar, S.K. Ghosh, P.S.V. Subba Rao, and V.R. Mamdapur Tetrahedron 48 1992 6897
14. T.K. Sarkar, B.K. Ghorai, and A. Banerji Tetrahedron Lett. 35 1994 6907
15. T.K. Sarkar, B.K. Ghorai, S.K. Nandy, B. Mukherjee, and A. Banerji J. Org. Chem. 62 1997 6006
16. T.K. Sarkar, B. Mukherjee, and S.K. Ghosh Tetrahedron 54 1998 3243
17. T.K. Sarkar, P. Gangopadhyay, B.K. Ghorai, S.K. Nandy, and J-M. Fang Tetrahedron Lett. 39 1998 8365
18. For the use of this terminology in ene reactions, see: (a) K. Mikami, and M. Shimizu Chem. Rev. 92 1992 1021
19. T.K. Sarkar J. Ind. Inst. Sci. 74 1994 329
20. E. Vedejs, and G.P. Meier Tetrahedron Lett. 20 1979 4185
21. M. Scartozzi, R. Grondin, and Y. Leblanc Tetrahedron Lett. 33 1992 5717
22. G.A. Kraus, and K. Neuenschwander Tetrahedron Lett. 21 1980 3841
23. Y. Nagao, W.M. Dai, M. Ochiai, and M. Shiro Tetrahedron 46 1990 6361
24. P.F. Keusenkothen, and M.B. Smith J. Chem. Soc., Perkin Trans. 1 1994 2485
25. Y.-M. Tsai, and B.-W. Ke J. Chin. Chem. Soc. 40 1993 641
26. Y.M. Tsai, B.-W. Ke, C.T. Yang, and C.-H. Lin Tetrahedron Lett. 33 1992 7895
27. For a preliminary communication, see: T.K. Sarkar, P. Gangopadhyay, and T.K. Satapathi Tetrahedron Lett. 40 1999 395
28. For synthesis of (±)-supinidine, see: (a) Y.-M. Tsai, B.-W. Ke, C.-T. Yang, and C.-H. Lin Tetrahedron Lett. 33 1992 7895
29. G.E. Keck, E.N.K. Cressman, and E.J. Enholm J. Org. Chem. 54 1989 4345
30. W.H. Pearson Tetrahedron Lett. 26 1985 3527
31. T. Hudlicky, J.O. Frazier, and L.D. Kwart Tetrahedron Lett. 26 1985 3523
32. D.A. Burnett, J.-K. Choi, D.J. Hart, and Y.-M. Tsai J. Am. Chem. Soc. 106 1984 8201
33. T. Kametani, K. Higashiyama, H. Otomasu, and T. Honda Heterocycles 22 1984 729
34. A.R. Chamberlin, H.D. Nguyen, and J.Y.L. Chung J. Org. Chem. 49 1984 1682
35. D.J. Hart, and T.-K. Yang Tetrahedron Lett. 23 1982 2761
36. A.R. Chamberlin, and J.Y.L. Chung Tetrahedron Lett. 23 1982 2619
37. D. Robins, and S. Sakdarat J. Chem. Soc. Perkin Trans. 1 1979 1734
38. J.J. Tufariello, and J.P. Tette J. Org. Chem. 40 1975 3866
39. (l) See also Ref. 7(d)
40. For synthesis of (-)-supinidine, see: (m) C.M. Boynton, A.T. Hewson, and D. Mitchell J. Chem. Soc., Perkin Trans. 1 2000 3599
41. P.G. Andersson, and J.E. Baeckvall J. Am. Chem. Soc. 114 1992 8696
42. H. Takahata, Y. Banba, and T. Momose Tetrahedron 47 1991 7635
43. Y. Nagao, W.M. Dai, M. Ochiai, and M. Shiro Tetrahedron 46 1990 6361
44. Y. Nagao, W.M. Dai, M. Ochiai, and M. Shiro Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 30 1988 468
45. Y. Nagao, W.M. Dai, and M. Ochiai Tetrahedron Lett. 29 1988 6133
46. D. Robins, and S. Sakdarat J. Chem. Soc. Perkin Trans. 1 1980 909
47. For synthesis of (±)-macronecine, see: (a) A.J. Aasen, and C.C.J. Culvenor J. Org. Chem. 34 1969 4143
48. A.J. Aasen, and C.C.J. Culvenor Chem. Commun. 1 1969 34
49. For synthesis of (-)-macronecine, see: (c) D.-C. Ha, J.-B. Ahn, and Y.-E. Kwon Bull. Kr. Chem. Soc. 19 1998 514
50. S.E. Denmark, and A.R. Hurd J. Org. Chem. 63 1998 3045
51. H. Ito, Y. Ikeuchi, T. Taguchi, Y. Hanzawa, and M. Shiro J. Am. Chem. Soc. 116 1994 5469
52. T.K. Sarkar, and S.K. Ghosh Tetrahedron Lett. 28 1987 2061
53. T.K. Sarkar, S.K. Ghosh, and T.K. Satapathi Tetrahedron 46 1990 1885
54. M. Fetizon, M. Golfier, R. Milcent, and I. Papadakis Tetrahedron 31 1975 165
55. J. Attenburrow, A.F.B. Cameron, J.H. Chapman, R.M. Evans, B.A. Hems, A.B.A. Jansen, and T. Walker J. Chem. Soc. 1952 1094
56. F.P.J.T. Rutjes, H. Hiemstra, H.H. Mooiweer, and W.N. Speckamp Tetrahedron Lett. 29 1988 6975
57. F.P.J.T. Rutjes, N.M. Teerhuis, H. Hiemstra, and W.N. Speckamp Tetrahedron 49 1993 8605
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J.A. Gaussian 98 revision A.5: Gaussian Inc., Pittsburgh, PA, 1998, USA.
59. I. Fleming, A. Barbero, and D. Walter Chem. Rev. 97 1997 2063
60. J. Sisko, J.R. Henry, and S.M. Weinreb J. Org. Chem. 58 1993 4945
61. T. Fukuyama, S.-C. Lin, and L. Li J. Am. Chem. Soc. 112 1990 7050
62. K. Asao, H. Iio, and T. Tokoroyama Tetrahedron Lett. 30 1989 6397
63. J.A. Dodge, J.I. Trujillo, and M. Presnell J. Org. Chem. 59 1994 234
64. S.E. Denmark, A. Thorarensen, and D.S. Middleton J. Am. Chem. Soc. 118 1996 8266