Construction of 8-Membered Ring Skeleton of Vinigrol via SmI2-Promoted Barbier Coupling

Synlett

Volumn 1997, Issue 2, 1997, Pages 219-220

  Kito, M ^a   Sakai, T ^a   Shirahama, H ^a   Miyashita, M ^a   Matsuda, F ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000619712     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-748     Document Type: Article

References (26)

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6. 2) has become an exceedingly useful reagent for promoting reductive coupling reactions in the last decade. For reviews, see: (a) Kagan, H.B. New J. Chem. 1990, 14, 453. (b) Molander, G.A. Chem. Rev. 1992, 92, 29. Molander, G.A.; Harris, R.H. Chem. Rev. 1996, 96, 307.
7. 2) has become an exceedingly useful reagent for promoting reductive coupling reactions in the last decade. For reviews, see: (a) Kagan, H.B. New J. Chem. 1990, 14, 453. (b) Molander, G.A. Chem. Rev. 1992, 92, 29. Molander, G.A.; Harris, R.H. Chem. Rev. 1996, 96, 307.
8. 2) has become an exceedingly useful reagent for promoting reductive coupling reactions in the last decade. For reviews, see: (a) Kagan, H.B. New J. Chem. 1990, 14, 453. (b) Molander, G.A. Chem. Rev. 1992, 92, 29. Molander, G.A.; Harris, R.H. Chem. Rev. 1996, 96, 307.
9. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
10. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
11. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
12. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
13. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
14. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
15. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
16. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
17. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
18. 2. See: (a) Kan, T.; Matsuda, F.; Yanagiya, M.; Shirahama, H. Synlett 1991, 391. (b) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158. Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111. Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532. (e) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900. (f) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729. (g) Matsuda, F. J. Synth. Org. Chem. Jpn. 1995, 53, 987. (h) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373. (i) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett, 1996, 1057. (j) Kawatsura, M.; Kishi, E.; Kito, M.; Sakai, T.; Shirahama, H.; Matsuda, F. Synlett, 1997, in press.
19. 2-promoted ketyl-olefin coupling (ref 5i).
20. Martinelli, M.J. J. Org. Chem. 1990, 55, 5065.
21. (+)-Chlorodihydrocarvone (2) was prepared by treatment of (+)-dihydrocarvone with HOCl. See: Hegde, S.G.; Bechwith, D.; Doti, R.; Wolinsky, J. J. Org. Chem. 1985, 50, 894.
22. 1′-H), 7.25-7.38 (5H, m, Ph).
23. 2, rt.
24. 2, rt.
25. 2, rt.
26. 2, rt.