Chiral diselenides in the total synthesis of (+)-samin

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2686-2689

  Wirth, Thomas ^a   Kulicke, Klaus J ^a   Fragale, Gianfranco ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

LIGNAN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS;

EID: 0030004036     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952093m     Document Type: Article

References (50)

1. Reviews: (a) MacRae, W. D.; Towers, G. H. N Phytochemistry, 1984, 23, 1207-1220. (b) Ayres, D. C,; Loike, J. D. Lignans: Chemical, biological and clinical properties; Cambridge University Press: Cambridge, 1990. (c) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205.
2. Reviews: (a) MacRae, W. D.; Towers, G. H. N Phytochemistry, 1984, 23, 1207-1220. (b) Ayres, D. C,; Loike, J. D. Lignans: Chemical, biological and clinical properties; Cambridge University Press: Cambridge, 1990. (c) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205.
3. Reviews: (a) MacRae, W. D.; Towers, G. H. N Phytochemistry, 1984, 23, 1207-1220. (b) Ayres, D. C,; Loike, J. D. Lignans: Chemical, biological and clinical properties; Cambridge University Press: Cambridge, 1990. (c) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205.
4. (a) Adriani, W. Z. Unters. Lebensm. 1928, 56, 187-194.
5. (b) Budowski, P. J. Am. Oil Chem. Soc. 1964, 41, 280-285.
6. Fukuda, Y.; Isobe, M.; Nagata, M.; Osawa, T.; Namiki, M. Heterocycles 1986, 24, 923-926.
7. (a) Ward, R. S. Tetrahedron 1990, 46, 5029-5041.
8. (b) Feringa, B. L.; de Lange, B.; Jansen, J. F. G. A.; de Jong, J. C.; Lubben, M.; Faber, W.; Schudde, E. P. Pure Appl. Chem. 1992, 64, 1865-1871.
9. (c) van Oeveren, A.; Jansen, J. F. G. A.; Fennga, B. L. J. Org. Chem. 1994, 59, 5999-6007.
10. (d) Ogiku, T.; Yoshida, S.; Otimizu, H.; Iwasaki, T. J. Org. Chem 1995, 60, 1148-1153.
11. (e) Yoshida, S.; Yamanaka, T.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 7271-7274.
12. (f) Suginome, H.; Orito, K.; Yorita, K.; Ishikawa, M.; Shimoyama, N.; Sasaki, T. J. Org. Chem. 1995, 60, 3052-3064.
13. (g) Pelter, A.; Ward, R. S. Heterocycles 1994, 137-147.
14. (h) Mikami, K.; Matsueda, H.; Nakai, T. Synlett 1993, 235-236.
15. (a) Takano, S.; Ohkawa, T.; Tamori, S.; Satoh, S.; Ogasawara, K. J Chem. Soc., Chem Commun. 1988, 189-191.
16. (b) Samizu, K.; Ogasawara, K. Chem. Lett. 1995, 543-544.
17. (a) Bradley, H. M.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1991, 1641-1643.
18. (b) Bradley, H. M.; Jones, R. G.; Knight, D. W. Synlett 1992, 479-480.
19. (c) Takano, S.; Samizu, K.; Ogasawara. K. J. Chem. Soc., Chem. Commun. 1993, 1032-1033.
20. (d) Takano, S.; Samizu, K., Ogasawara, K. Synlett 1993, 785-787
21. (e) Maiti, G.; Adhikari, S.; Roy, S C. Tetrahedron Lett. 1994, 35, 6731-6732.
22. (f) Maiti, G.; Adhikan, S.; Roy, S. C. Tetrahedron 1995, 51, 8389-8396.
23. Wirth, T. Angew Chem , Int. Ed. Engl. 1995, 34, 1726-1728. Angew Chem. 1995, 107, 1872-1873.
24. Wirth, T. Angew Chem , Int. Ed. Engl. 1995, 34, 1726-1728. Angew Chem. 1995, 107, 1872-1873.
25. (a) Dervant, R. M.; Radunz, H. E. In Houben-Weyl, Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme; Stuttgart, 1995; Vol. E 21 b; p 1314.
26. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
27. Wirth, T.; Kulicke, K. J. Unpublished results. Recent NMR investigations have shown, that the Se-Se bond is cleaved rapidly and the active catalyst is a selenolate coordinated to zinc. Similar sulfur systems have been reported: (a) Rijnberg, E.; Jastrzebski, J. T. B. H.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524. (b) Hof. R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34. (c) Fitzpatnck, K; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
28. Wirth, T.; Kulicke, K. J. Unpublished results. Recent NMR investigations have shown, that the Se-Se bond is cleaved rapidly and the active catalyst is a selenolate coordinated to zinc. Similar sulfur systems have been reported: (a) Rijnberg, E.; Jastrzebski, J. T. B. H.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524. (b) Hof. R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34. (c) Fitzpatnck, K; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
29. Wirth, T.; Kulicke, K. J. Unpublished results. Recent NMR investigations have shown, that the Se-Se bond is cleaved rapidly and the active catalyst is a selenolate coordinated to zinc. Similar sulfur systems have been reported: (a) Rijnberg, E.; Jastrzebski, J. T. B. H.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524. (b) Hof. R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34. (c) Fitzpatnck, K; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
30. Wirth, T.; Kulicke, K. J. Unpublished results. Recent NMR investigations have shown, that the Se-Se bond is cleaved rapidly and the active catalyst is a selenolate coordinated to zinc. Similar sulfur systems have been reported: (a) Rijnberg, E.; Jastrzebski, J. T. B. H.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524. (b) Hof. R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34. (c) Fitzpatnck, K; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
31. Wirth, T. Tetrahedron Lett. 1995, 36, 7849-7852.
32. Baba, N.; Nishiyama, K.; Oda, J.; Inouye, Y.Agric. Biol. Chem. 1976, 40, 1441-1443.
33. van Koten, G.; Jastrzebski, J. T. B. H. Tetrahedron 1989, 45, 569-578.
34. Meyer, N.; Seebach, D. Chem. Ber. 1980, 113, 1304-1319.
35. (a) Déziel, R.; Malenfant, E. J. Org. Chern. 1995, 60, 4660-4662.
36. (b) Fukuzawa, S.; Kasugahara, Y. Tetrahedron Lett. 1994, 35, 9403-9406.
37. (c) Fujita, K.; Murata, K.: Iwaoka, M.; Tomoda, S. Tetrahedron Lett. 1995, 36, 5219-5222.
38. Kanematsu, K.; Tsuruoka, M.; Takaoka, Y.; Sasaki, T. Heterocycles 1991, 32, 859-862.
39. Adegoke, E. A.; Emokpae, T. A.; Ephraim-Bassey, H. J. Heterocycl. Chem. 1986, 23, 1195-1198.
40. Propargylic alcohol can be used as nucleophile as well, but the yield of the addition reaction is lower (20%) and the subsequent radical cyclization to the already known tetrahydrofuran intermediate [lit 6e.f] less efficient (29%).
41. (a) Apparu, M.; Crandall, J. K. J. Org. Chem. 1984, 49. 2125-2130.
42. (b) Burnett, D. A.; Choi, J.; Hart, D. J.; Tsai, Y J. Am. Chem. Soc. 1984, 706, 8201-8209.
43. (a) Lubbers. T.; Schafer, H. J. Synlett 1990, 44-46.
44. (b) Lubbers, T.; Schafer, H. J. Synlett 1991, 861-862.
45. (c) Baldwin, J. E.; Li, C. J. Chem. Soc., Chem. Commun, 1987, 166-168.
46. (a) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. in Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1996; Vol. 48, p 301.
47. (b) Curran, D. P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions; Verlag Chemie: Weinheim, 1996.
48. RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139-145.
49. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
50. The treatment with sodium methoxide was wrongly reported to yield the 3.4-cis-isomer. [lit. 6d-f].