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Volumn 65, Issue 12, 2000, Pages 3869-3874

A straightforward route to stereodefined functionalized cycloheptanols and cyclooctanols

Author keywords

[No Author keywords available]

Indexed keywords

HEPTANOL; OCTANOL;

EID: 0034674424     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0000224     Document Type: Article
Times cited : (19)

References (81)
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1999) Tetrahedron Lett. , pp. 1375
    • Montana, A.M.1    Garcia, F.2    Grima, P.M.3
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10976
    • Wender, P.A.1    Rieck, H.2    Fuji, M.3
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    • 0032511385 scopus 로고    scopus 로고
    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7995
    • Renaud, J.1    Quellet, S.G.2
  • 11
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1940
    • Wender, P.A.1    Husfeld, C.O.2    Langkopf, E.3    Love, J.A.4
  • 12
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) J. Org. Chem. , vol.63 , pp. 4732
    • Snider, B.B.1    Vo, N.H.2    O'Neil, S.V.3
  • 13
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) J. Org. Chem. , vol.63 , pp. 4164
    • Wender, P.A.1    Sperandio, D.2
  • 14
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) Chem. Commun. , pp. 2251
    • Hall, A.1    Bailey, P.D.2    Rees, D.C.3    Wightman, R.H.4
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7889
    • Lee, P.H.1    Lee, J.2
  • 16
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8355
    • Kotora, M.1    Umeda, C.2    Ishida, T.3    Takahashi, T.4
  • 17
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    • Recent references of seven-membered-ring syntheses: (a) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 5811. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (c) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129. (d) Montana, A. M.; Garcia, F.; Grima, P. M. Tetrahedron Lett. 1999, 1375. (e) Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976. (f) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (h) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732. (i) Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164. (j) Hall, A.; Bailey, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889. (l) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355. (m) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (n) Review: Harmata, M. Tetrahedron 1997, 53, 6235. (o) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8299
    • Hikichi, S.1    Hareau, G.P.-J.2    Sato, F.3
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