Synthesis of cyclohexenols and cycloheptenols via the regioselective reductive ring opening of oxabicyclic compounds

Journal of the American Chemical Society

Volumn 119, Issue 28, 1997, Pages 6478-6487

  Lautens, Mark ^a   Ma, Shihong ^a   Chiu, Pauline ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030810474     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964361j     Document Type: Article

References (44)

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5. For recent reviews of metal-catalyzed hydrosilation, see: (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 763. (b) Mikolajczyk, M.; Drabowicz, J.; Kielbasinski, P. Stereoselective Synthesis; Houben-Weyl, 4th ed.; E21e, p 5733.
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7. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
8. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
9. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
10. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
11. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
12. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
13. Metal-catalyzed hydrostannation: (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. (b) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881. (c) Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857. (d) Miyake, H.; Yamamuram, K. Chem. Lett. 1991, 1099. (e) Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187. (f) Casson, S.; Kocienski, P. Synthesis 1993, 1133. (g) Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329 and references therein.
14. For a recent review of alkene and alkyne hydroalumination, see: Eisch, J. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, p 733.
15. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
16. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
17. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
18. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
19. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
20. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
21. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
22. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
23. For reviews describing the synthesis, reactions, and utility of oxabicyclic compounds, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 3. (b) Keay, B. A.; Woo, S. Synthesis 1996, 669. (c) Shipman, M. Contemp. Org. Synth. 1995, 2 (1), 1. (d) Lautens, M. Synlett 1993, 177. (e) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (f) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. (g) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. (h) Harmata, M. In Advances in Cycloadditions; Lautens, M., Ed.; JAI Press: Greenwich, CT; Vol. 4, p 41. (i) West, F. G. Ibid; p 1.
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