A new synthetic approach to the carbocyclic core of cyclopentane-type glycosidase inhibitors: Asymmetric synthesis of aminocyclopentitols via free radical cycloisomerization of enantiomerically pure alkyne-tethered oxime ethers derived from carbohydrates

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1354-1358

  Marco Contelles, José ^a   Destabel, Christine ^a   Gallego, Pilar ^a   Chiara, José Luis ^a   Bernabé, Manuel ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5 ACETAMIDO 1 ACETOXYMETHYL 2,3,4 TRI O ACETYLCYCLOPENTANE 1,2,3,4 TETRAOL; CYCLOPENTANE DERIVATIVE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029915402     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951891+     Document Type: Article

References (80)

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16. Although the free radical cyclization of terminal alkynes with oxime ethers has been known for some years, its high synthetic potential has been almost neglected: (a) Enholm, E. J., Burroff, J. A.; Jaramilln, L. M. Tetrahedron Lett. 1990, 31, 3727. For the analogous cyclization of β-allenic oxime ethers, see: (b) Hatem, J.; Henriet-Bernard, C ; Grimaldi, J.; Maurin, R. Tetrahedron Lett. 1992, 33, 1057.
17. A preliminary account of this work has been published: Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabé, M. Tetrahedron: Asymmetry 1995, 6, 1547.
18. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
19. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
20. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
21. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
22. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
23. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
24. For some recent synthetic approaches, see reference 8 and the following: (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253. (b) Gallos, J. K.; Goga, E. G., Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1 1994, 613. (c) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361. (d) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1993, 34, 7895. (e) Marco-Contelles, J.; Ruiz, P.; Martínez. L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. (f) Elliot, R. P.; Hui, A.; Fairbanks, A J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949. (g) Chiara, J. L ; Marco-Contelles, Khiar, N.; Destabel, C.; Gallego, P.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
25. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
26. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
27. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
28. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
29. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
30. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
31. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
32. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
33. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
34. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
35. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
36. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
37. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
38. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
39. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
40. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
41. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. For the synthesis of some representative examples of cyclopentane glycosidase inhibitors, see the following references. Mannostatins: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Ganem, B. King, S. B J. Am. Chem. Soc. 1991, 113, 5089. (c) Trost, B.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317. (d) Ogawa, S.; Yuming, Y. J. Chem. Soc., Chem Commun. 1991, 890. (e) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. Allosamizoline-the cyclopentane component of Allosamidine-: (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Simpkins, N. S.; Stokes, S.; Whittle, A. Tetrahedron Lett. 1992, 33, 793. (h) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123. (j) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444. (k) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1991, 113, 5863. Trehalostatin: (l) Uchida, C.; Yamagagishi, T.; Ogawa, S. Chem. Lett. 1993, 971. Trehazolin: (m) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065. (n) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. Merrell-Dow cyclopentylamine: (o) Farr, R. A.; Peet, N. P.; Kang, M. S. Tetrahedron Lett. 1990, 31, 7109.
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70. 2 seems to be unprecedented. For the first very recent reports on the nitrogen-oxygen samarium diiodide-mediated cleavage, see refs 5, 6g, and the following: (a) Chiara, J. L.; Destabel. C.; Gallego, P.; Marco-Contelles, J. J Org. Chem. 1996, 61, 359. (b) Keck, G. E.; McHardy, S. F ; Murry, J. A. J. Am. Chem. Soc 1995, 117, 7289. (c) Keck, G. E.; McHardy, S F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419 (personal communication; we thank Professor Keck for sending us a copy of this manuscript prior to publication).
71. 2 seems to be unprecedented. For the first very recent reports on the nitrogen-oxygen samarium diiodide-mediated cleavage, see refs 5, 6g, and the following: (a) Chiara, J. L.; Destabel. C.; Gallego, P.; Marco-Contelles, J. J Org. Chem. 1996, 61, 359. (b) Keck, G. E.; McHardy, S. F ; Murry, J. A. J. Am. Chem. Soc 1995, 117, 7289. (c) Keck, G. E.; McHardy, S F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419 (personal communication; we thank Professor Keck for sending us a copy of this manuscript prior to publication).
72. 2 seems to be unprecedented. For the first very recent reports on the nitrogen-oxygen samarium diiodide-mediated cleavage, see refs 5, 6g, and the following: (a) Chiara, J. L.; Destabel. C.; Gallego, P.; Marco-Contelles, J. J Org. Chem. 1996, 61, 359. (b) Keck, G. E.; McHardy, S. F ; Murry, J. A. J. Am. Chem. Soc 1995, 117, 7289. (c) Keck, G. E.; McHardy, S F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419 (personal communication; we thank Professor Keck for sending us a copy of this manuscript prior to publication).
73. 2 seems to be unprecedented. For the first very recent reports on the nitrogen-oxygen samarium diiodide-mediated cleavage, see refs 5, 6g, and the following: (a) Chiara, J. L.; Destabel. C.; Gallego, P.; Marco-Contelles, J. J Org. Chem. 1996, 61, 359. (b) Keck, G. E.; McHardy, S. F ; Murry, J. A. J. Am. Chem. Soc 1995, 117, 7289. (c) Keck, G. E.; McHardy, S F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419 (personal communication; we thank Professor Keck for sending us a copy of this manuscript prior to publication).
74. We have found also that the direct osmylation or epoxidation of vinyl derivative 20 (Scheme 5) proved unsuccessful.
75. (a) Ganem, B.; King, S. B. J. Am. Chem. Soc. 1994, 116, 562.
76. (b) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. J. Am. Chem. Soc. 1988, 110, 621.
77. 4 does not take place in the hydroxylation of certain acyclic sulfoxide-substituted allylic amides: Hauser, F. M.; Ellenberger, S. R.; Clardy, J. C.; Bass, L. S. J. Am. Chem. Soc. 1984, 106, 2458.
78. 4 does not take place in the hydroxylation of certain acyclic sulfoxide-substituted allylic amides: Hauser, F. M.; Ellenberger, S. R.; Clardy, J. C.; Bass, L. S. J. Am. Chem. Soc. 1984, 106, 2458.
79. Chen, S.-M. L.; Schaub, R. E.; Grudzinskas, C. V. J. Org. Chem. 1978, 43, 3450.
80. Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 3535.