1,3-asymmetric induction in electrophilic addition onto homoallylsilanes. An approach towards the total synthesis of (+/-)-kumausyne

Tetrahedron

Volumn 53, Issue 8, 1997, Pages 2835-2854

  Audrey, Olivier ^a   Glanzmann, Cécile ^a   Landais, Yannick ^a   Parra Rapado, Liliana ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

KUMAUSYNE; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584879     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00003-3     Document Type: Article

References (66)

1. 1. (a) Labelle, M.; Morton, H.E.; Guindon, Y.; Springer, J.P. J. Am. Chem. Soc., 1988, 110, 4533-4540 and references cited therein;
2. (b) Bravo, P.; Resnati, G.; Viani, F.; Arnone, A. J. Chem. Soc., Perkin Trans I, 1989, 839-840;
3. (c) Bartlett, P.A.; Richardson, D.P.; Myerson, J. Tetrahedron, 1984, 40, 2317-2327;
4. (d) Bedford, S.B.; Fenton, G.; Knight, D.W.; Shaw, D. Tetrahedron Lett., 1992, 33, 6505-6506;
5. (e) Bennett, F.; Bedford, S.B.; Bell, K.E.; Fenton, G.; Knight, D.W.; Shaw, D. Ibid., 1992, 33, 6507-6510;
6. (f) Bedford, S.B.; Bell, K.E.; Fenton, G.; Hayes, C.J.; Knight, D.W.; Shaw, D. Ibid., 1992, 33, 6511-6514;
7. (g) Kang, S.H.; Hwang, T.S.; Kim, W.J.; Lim, J.K. Ibid., 1990, 31, 5917-5920;
8. (h) Kang, S.H.; Lee, S.B. Ibid., 1993, 34, 1955-1958;
9. (i) Fleming, I.; Lawrence N.J. J. Chem. Soc., Perkin Trans I, 1992, 3309-3326;
10. (j) Knight, D.W.; Shaw, D.; Fenton, G. Synlett, 1994, 295-296;
11. (k) Kang, S.H.; Lee, S.B. Tetrahedron Lett., 1993, 34, 7579-7582;
12. (l) Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Ibid., 1992, 33, 1747-1748;
13. (m) Evans, P.A.; Roseman, J.D. Ibid., 1995, 36, 31-34;
14. (n) Lipshutz, B.H.; Tirado, R. J. Org. Chem., 1994, 59, 8307-8311.
15. 2. (a) Reitz, A.B.; Nortey, S.O.; Maryanoff, B.E.; Liotta, D.; Monahan, R., III J. Org. Chem., 1987, 52, 4191-4202;
16. (b) Tamaru, Y.; Kawamura, S.; Yoshida, Z. Ibid., 1985, 26, 2885-2888;
17. (c) Pougny, J.R.; Nassr, M.A.M.; Sinay, P. J. Chem. Soc., Chem. Commun., 1981, 375-376;
18. (d) Chamberlin, A.R.; Dezube, M.; Dussault, P.; McMills, M.C. J. Am. Chem. Soc., 1983, 105, 5819-5825;
19. (e) Labelle, M.; Guindon, Y. Ibid., 1989, 111, 2204-2210;
20. (f) Tamaru, Y.; Hojo, M.; Kawamura, S.; Sawada, S.; Yoshida, Z. J. Org. Chem., 1987, 52, 4062-4072;
21. (g) Semmelhack, M.F.; Zhang, N. Ibid., 1989, 54, 4483-4485;
22. (h) Chamberlin, A.R.; Mulholland, R.L., Jr.; Kahn, S.D.; Hehre, W.J. J. Am. Chem. Soc., 1987, 109, 672-677;
23. (i) Mihelich, E.D.; Hite, G.A. Ibid., 1992, 114, 7318-7319.
24. 3. For reviews on the subject, see: (a) Boivin, T.L.B. Tetrahedron, 1987, 43, 3309-3362;
25. (b) Cardillo, G.; Orena, M. Ibid., 1990, 46, 3321-3408 and references cited therein;
26. (c) Bartlett, P.A. Asymmetric Synthesis, Morrison, J.D., Eds.; Academic Press: New York, 1984; vol 3, pp. 411-454.
27. 4. (a) Andrey, O.; Landais, Y.; Planchenault, D. Tetrahedron Lett., 1993, 34, 2927-2930;
28. (b) Landais, Y.; Planchenault, D. Tetrahedron Lett., 1994, 35, 4565-4568;
29. (c) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1994, 35, 9549-9552.
30. 5. For a preliminary communication, see: Andrey, O.; Landais, Y. Tetrahedron Lett., 1993, 34, 8435-8438.
31. 6. For reviews on the use of the silicon group as a masked hydroxy group, see: (a) Fleming, I. Chemtracts, Org. Chem., 1996, 9, 1-64;
32. (b) Jones, G.R.; Landais, Y. Tetrahedron, 1996, 52, 7599-7662.
33. 7. 4a is commercially available (Fluka). 4b-c have been prepared using a reported procedure, see: Andrey, O.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1995, 51, 12083-12096.
34. 8. Larock, R.C. Solvomercuration - Demercuration reactions in Organic Synthesis; Eds.; Springer Verlag: Berlin Heidelberg, 1986; pp. 88.
35. 9. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press: Oxford, 1986.
36. 10. (a) Brown, H.C.; Kurek, J.T.; Rei, M.-H.; Thompson, K.L. J. Org. Chem., 1984, 49, 2551-2557;
37. (b) Brown, H.C.; Geoghegan, P.J.; Kurek, J.T. J. Org. Chem., 1981, 46, 3810-3812.
38. 11. For studies about kinetic vs thermodynamic control for related reactions, see: (a) Harding, K.E.; Marman, T.H. J. Org. Chem., 1984, 49, 2838-2840;
39. (b) Harding, K.E.; Marman, T.H.; Nam, D. Tetrahedron Lett., 1988, 29, 1627-1630;
40. (c) Bartlett, P.A.; Myerson, J. J. Am. Chem. Soc., 1978, 100, 3950-3952.
41. 12. Harding, K.E.; Burks, S.R. J. Org. Chem., 1981, 46, 3920-3922.
42. C-Si bond of a developing charge in the γ position relative to the silicon group (Silicon-γ-effect) have appeared and therefore electronic effects cannot be excluded, see: Shiner, V.J., Jr.; Ensinger, M.W.; Rutkowske, R.D. J. Am. Chem. Soc., 1987, 109, 804-809 and references cited.
43. 14. Faulkner, D.J. Nat. Prod. Rep., 1992, 9, 323-364 and references cited therein.
44. 15. (a) Erickson, F.L. Marine Natural Products; Scheuer, P.J., Eds.; Academic Press: New York, 1986; Vol 5, pp. 131-257;
45. (b) Fukuzawa, A.; Aye, M.; Murai, A. Chem. Lett., 1990, 1579-1580;
46. (c) Fukuzawa, A.; Takasugi, Y.; Murai, A. Tetrahedron Lett., 1991, 32, 5597-5598;
47. (d) Fukuzawa, A.; Aye, M.; Nakamura, M.; Tamura, M.; Murai, A. Chem. Lett., 1990, 1287-1290;
48. (e) Ishihara, J.; Kanoh, N.; Murai, A. Tetrahedron Lett., 1995, 36, 737-740.
49. 16. For total synthesis of 3, see: (a) Grese, T.A.; Hutchinson, K.D.; Overman, L.E. J. Org. Chem., 1993, 58, 2468-2477;
50. (b) Brown, M.J.; Harrison, T.; Overman, L.E. J. Am. Chem. Soc., 1991, 113, 5378-5384;
51. (c) Osumi, K.; Sugimura, H. Tetrahedron Lett., 1995, 36, 5789-5792; For a synthetic approach, see:
52. (d) Tonn, C.E.; Polazòn, J.M.; Ruiz-Pérez, C.; Rodriguez, M.L.; Martìn, V.S. Tetrahedron Lett., 1988, 29, 3149-3152.
53. 17. (a) Hudrlik, P.F.; Peterson, D. J. Am. Chem. Soc., 1975, 97, 1464-1468;
54. (b) Enders, D.; Nakai, S. Helv. Chim. Acta, 1990, 73, 1833-1836;
55. (c) Enders, D.; Nakai, S. Chem. Ber., 1991, 124, 219-226.
56. 18. For reports concerning mercuri-mediated cyclization of dienols, such as linalool and nerolidol, see: (a) Matsuki, Y.; Kodama, M.; Itô, S. Tetrahedron Lett., 1979, 2901-2904;
57. (b) Matsuki, Y.; Kodama, M.; Itô, S. Tetrahedron Lett., 1979, 4081-4084.
58. 19. Jeffery, T. Tetrahedron Lett., 1989, 30, 2225-2228.
59. 20. (a) Vig, O.P.; Sharma, M.L.; Sabharwal, A.; Gupta, R.; Huq, M.A. J. Indian Chem. Soc., 1990, 67, 34-36;
60. (b) Chin, S.K.; Golding, B.T.; Pierpoint, C. J. Chem. Res. (S), 1985, 71-71;
61. (c) Jacoby, D.; Célérier, J.-P.; Petit, H.; Lhommet, G. Synthesis, 1990, 301-304.
62. 21. Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1995, 36, 2987-2990.
63. 22. (a) Larson, G.L. Pure & Appl. Chem., 1990, 62, 2021-2026, and references cited therein;
64. (b) Larson, G.L.; Hernandez, D. J. Org. Chem., 1984, 49, 4285-4287.
65. 23. Seyden-Penne, J., Reductions by the Alumino-and Borohydrides in Organic Synthesis, VCH publishers, Inc., 1991, 125.
66. 24. For studies concerning this problem, see the following communication in this issue.