Extremely convenient cyclization of medium rings using SmI2

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 863-864

  Matsuda, Fuyuhiko ^a   Sakai, Toshinari ^a   Okada, Naoko ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NATURAL PRODUCT;

ARTICLE; CHEMISTRY; CONTROLLED STUDY; CYCLIZATION; JAPAN; NONHUMAN; TECHNIQUE; TEMPERATURE;

EID: 0032546078     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10750-X     Document Type: Article

References (24)

1. (1) For review, see: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
2. 2) has become an exceedingly useful reagent for promoting reductive coupling reactions. For reviews, see: (a) Kagan, H. B. New J. Chem. 1990, 14, 453.
3. (b) Molander, G. A. Chem. Rev. 1992, 92, 29.
4. (c) Molander, G. A.; Harris, R. H. Chem. Rev. 1996, 96, 307.
5. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391.
6. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158.
7. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111.
8. (d) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532.
9. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900.
10. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729.
11. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987.
12. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373.
13. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057.
14. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett 1997, 479.
15. 2-mediated Reformatsky reactions, ketone-olefin reductive couplings, and pinacol couplings have been adapted to permit construction of medium ring molecules. See: (a) Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889.
16. (b) Inanaga, J.; Yokoyama, Y.; Handa, Y.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 6371.
17. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186.
18. (d) Shiina, I.; Uoto, K.; Mori, N.; Kosugi, T.; Mukaiyama, T. Chem. Lett. 1995, 181.
19. (e) Swindell, C. S.; Fan, W. Tetrahedron Lett. 1996, 37, 2321.
20. 2-promoted cyclization of medium rings as described in the text. In contrast, 7-chloromethyl-7-octenal gave a mixture of unidentified products without any formation of the 8-membered ring product.
21. (6) Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219.
22. (7) (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763.
23. (b) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
24. (c) Otsubo, K.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 1487.