Synthesis of aminocyclitols by intramolecular reductive coupling of carbohydrate derived δ- and ε-functionalized oxime ethers promoted by tributyltin hydride or samarium diiodide

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7397-7412

  Marco Contelles, José ^a   Gallego, Pilar ^a   Rodríguez Fernández, Mercedes ^a   Khiar, Noureddine ^a,b   Destabel, Christine ^a   Bernabé, Manuel ^a   Martínez Grau, Angeles ^a,c   Chiara, Jose Luis ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5' NORARISTEROMICIN; ALLOSAMIDIN; AMINOCYCLITOL; ARISTEROMYCIN; MANNOSTATIN A; NEPLANOCIN A; SAMARIUM DIIODIDE; TREHAZOLIN; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; MOLECULAR RECOGNITION; SEQUENCE ANALYSIS; STEREOCHEMISTRY;

EID: 0030780809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970987w     Document Type: Article

References (101)

1. Recent syntheses: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444, and references cited therein. (c) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562, and references cited therein, (d) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. (e) Ogawa, S.; Kimura, H.; Uchida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1695, and references cited therein.
2. Recent syntheses: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444, and references cited therein. (c) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562, and references cited therein, (d) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. (e) Ogawa, S.; Kimura, H.; Uchida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1695, and references cited therein.
3. Recent syntheses: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444, and references cited therein. (c) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562, and references cited therein, (d) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. (e) Ogawa, S.; Kimura, H.; Uchida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1695, and references cited therein.
4. Recent syntheses: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444, and references cited therein. (c) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562, and references cited therein, (d) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. (e) Ogawa, S.; Kimura, H.; Uchida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1695, and references cited therein.
5. Recent syntheses: (a) Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096. (b) Trost, B. M.; Van Kranken, D. L. J. Am. Chem. Soc. 1993, 115, 444, and references cited therein. (c) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562, and references cited therein, (d) Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121. (e) Ogawa, S.; Kimura, H.; Uchida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1695, and references cited therein.
6. Recent syntheses of trehazoline and its aglycon: (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813, and references therein, (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans 1 1994, 589, and references cited therein. (c) Knapp. S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
7. Recent syntheses of trehazoline and its aglycon: (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813, and references therein, (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans 1 1994, 589, and references cited therein. (c) Knapp. S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
8. Recent syntheses of trehazoline and its aglycon: (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813, and references therein, (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans 1 1994, 589, and references cited therein. (c) Knapp. S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
9. Recent syntheses of trehazoline and its aglycon: (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813, and references therein, (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans 1 1994, 589, and references cited therein. (c) Knapp. S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
10. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
11. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
12. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
13. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
14. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
15. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
16. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
17. Recent syntheses of allosamidine and its aglycon: (a) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565, and references cited therein, (c) Simpkins, N. S.; Stokes, S.; Whittle, A. J. Chem. Soc., Perkin Trans. 1 1992, 2471, and references cited therein, (d) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci., Biotechnol., Biochem. 1993, 57, 1906. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; Van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515. (f) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997. (g) Blattner, R.; Furneaux, R. H.; Kemmit, T.; Tyler, P. C.; Ferrier, R.; Tidén, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411. (h) Griffith, D. A.; Danishefsky, S. J. Am. Chem. Soc. 1996, 118, 9526, and references cited therein. See also ref 1b.
18. For a review, see: Quinkert, E., Ed. Synform 1989, 7, 192.
19. For a review, see: Quinkert, E., Ed. Synform 1989, 7, 225.
20. (a) Siddiqi, S. M.; Chen, X.; Schneller, S. W. J. Med. Chem. 1994, 37, 1382.
21. (b) Siddiqi, S. M.; Chen, X.; Schneller, S. W. J. Med. Chem. 1994, 37, 551, and references cited therein.
22. Aminoglycoside antibiotics; Umezawa, H., Hooper, I. R., Eds.; Springer-Verlag: New York, 1982.
23. For a recent review on the use of carbohydrate templates for the preparation of carbocycles, see: Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
24. (a) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631.
25. (b) Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 120, 1633. For recent examples, see: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499, and references cited therein.
26. (b) Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 120, 1633. For recent examples, see: Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499, and references cited therein.
27. (a) Kim, S.; Kee, I. S. Tetrahedron. Lett. 1993, 34, 4213.
28. (b) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447.
29. (c) Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514.
30. (d) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron Lett. 1994, 35, 6369.
31. Kim, S.; Yoon, K. S.; Kim, Y. S. Tetrahedron 1997, 53, 73.
32. (a) Marco-Contelles, J.; Martínez, L.; Martínez-Grau, A. Tetrahedron: Asymmetry 1991, 2, 961.
33. (b) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. For a later report on exactly the same methodology, see: Ingall, A. H.; Moore, P. R.; Roberts, S. M. Chem. Commun. 1994, 83 (corrigendum: Chem. Commun. 1994, 675).
34. (b) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. For a later report on exactly the same methodology, see: Ingall, A. H.; Moore, P. R.; Roberts, S. M. Chem. Commun. 1994, 83 (corrigendum: Chem. Commun. 1994, 675).
35. (b) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669. For a later report on exactly the same methodology, see: Ingall, A. H.; Moore, P. R.; Roberts, S. M. Chem. Commun. 1994, 83 (corrigendum: Chem. Commun. 1994, 675).
36. (c) Marco-Contelles, J.; Sánchez, B. J. Org. Chem. 1993, 58, 4293.
37. (d) Marco-Contelles, J.; Destabel, C.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1996, 61, 1354.
38. (e) Marco-Contelles, J. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, in press.
39. (a) Chiara, J. L.; Martin-Lomas, M. Tetrahedron Lett. 1994, 35, 2969.
40. (b) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1547.
41. (c) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
42. (d) Chiara, J. L.; Martinez, S.; Bernabé, M. J. Org. Chem. 1996, 61, 6488.
43. (e) Chiara, J. L. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; VCH: Weinheim, in press.
44. For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46, 211. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
45. For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46, 211. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
46. For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46, 211. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
47. (a) Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546.
48. For a similar cyclization using samarium diiodide, see: (b) Zhou, Z.; Bennett, S. M. Tetrahedron Lett. 1997, 38, 1153.
49. See also: (c) RajanBabu, T. V. J. Org. Chem. 1988, 53, 4522.
50. Yeung, B. W.; Alonso, R.; Vité, G. D.; Fraser-Reid, B. J. Carbohydr. Chem. 1989, 8, 413, and references cited therein.
51. 3,4 = 0 Hz clearly suggested a trans relative stereochemistry for these carbons, establishing as R the absolute configuration at the new stereocenter.
52. 1H NMR and 2D NOESY studies (see the Supporting Information),
53. HC(NHOBn)-HC(OTBS) = 9.4 Hz; this value strongly suggets a trans arrangement between these vicinal protons, establishing as R the absolute configuration at the new stereocenter.
54. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
55. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073 and references therein.
56. (a) Chiara, J. L.; Destabel, C.; Gallego, P.; Marco-Contelles, J. J. Org. Chem. 1996, 61, 359.
57. (b) Keck, G. E.; McHardy, S. F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419.
58. 3) δ 8.28 and 8.23 (2s, 2H), 5.18 (m, 1H), 4.71 (m, 2H), 4.33 (t, J - 4.2 Hz, 1H), 2.55 (m, 2H). Chemial equation presents
59. 2 cannot be discarded.
60. In fact, in these reactions we detect always benzyl alcohl that results from the N-O reductive cleavage. The presence of HMPA made troublesome to isolate, for instance, the corresponding amino alcohol 26 (Scheme 4).
61. Shen, S. Y.; Jouillé, M. M. J. Org. Chem. 1984, 49, 2168. Bagget, N.; Buchanan, J. G.; Fatah, M. Y.; Lachut, C. H.; McCullough, K. J.; Webber, J. M.; J. Chem. Soc., Chem. Commun. 1985, 1826.
62. Shen, S. Y.; Jouillé, M. M. J. Org. Chem. 1984, 49, 2168. Bagget, N.; Buchanan, J. G.; Fatah, M. Y.; Lachut, C. H.; McCullough, K. J.; Webber, J. M.; J. Chem. Soc., Chem. Commun. 1985, 1826.
63. (a) Enholm, E. J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463.
64. (b) Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5841.
65. (c) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1994, 35, 1627.
66. (d) Tadano, K.-i.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266, and references cited therein.
67. Aurrecoechea has recently described a related aproach using α-benzotriazolylalkenylamines: (a) Aurrecoechea, J. M.; Fernández-Acebes, A. Tetrahedron Lett. 1993, 34, 549. (b) Aurrecoechea, J. M.; López, B.; Fernández, A.; Arrieta, A.; Cossío, F. P. J. Org. Chem. 1997, 62, 1125.
68. Aurrecoechea has recently described a related aproach using α-benzotriazolylalkenylamines: (a) Aurrecoechea, J. M.; Fernández-Acebes, A. Tetrahedron Lett. 1993, 34, 549. (b) Aurrecoechea, J. M.; López, B.; Fernández, A.; Arrieta, A.; Cossío, F. P. J. Org. Chem. 1997, 62, 1125.
69. Fry, A. J.; Little, R. D.; Leonetti, J. J. Org. Chem. 1994, 59, 5017.
70. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 2821.
71. (a) Shono, T.; Rise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525.
72. (b) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730.
73. (a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205.
74. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T. Tetrahedron Lett. 1995, 36, 253.
75. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555.
76. Lactols 40 and 41 were easily obtained in two steps from the corresponding free sugar: Decoster, E.; Lacombe, J.-M.; Strebler, J.-L.; Ferrari, B.; Pavia, A. A. J. Carbohydr. Chem. 1983, 2, 329. Lactol 42 cannot be prepared using this methodology, and it was in turn obtained from the corresponding thiophenyl glycoside (Garegg, P. J.; Hultberg, H.; Lindberg, C. Carbohydr. Res. 1980, 83, 157) by oxidative hydrolysis with NBS in aqueous acetone: Groneberg, R. D.; Miyasaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwasbuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593 (for an analogous hydrolysis procedure, see: Motavia, M. S.; Marcussen, J.; Moller, B. L. J. Carbohydr. Chem. 1995, 14, 1279).
77. Lactols 40 and 41 were easily obtained in two steps from the corresponding free sugar: Decoster, E.; Lacombe, J.-M.; Strebler, J.-L.; Ferrari, B.; Pavia, A. A. J. Carbohydr. Chem. 1983, 2, 329. Lactol 42 cannot be prepared using this methodology, and it was in turn obtained from the corresponding thiophenyl glycoside (Garegg, P. J.; Hultberg, H.; Lindberg, C. Carbohydr. Res. 1980, 83, 157) by oxidative hydrolysis with NBS in aqueous acetone: Groneberg, R. D.; Miyasaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwasbuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593 (for an analogous hydrolysis procedure, see: Motavia, M. S.; Marcussen, J.; Moller, B. L. J. Carbohydr. Chem. 1995, 14, 1279).
78. Lactols 40 and 41 were easily obtained in two steps from the corresponding free sugar: Decoster, E.; Lacombe, J.-M.; Strebler, J.-L.; Ferrari, B.; Pavia, A. A. J. Carbohydr. Chem. 1983, 2, 329. Lactol 42 cannot be prepared using this methodology, and it was in turn obtained from the corresponding thiophenyl glycoside (Garegg, P. J.; Hultberg, H.; Lindberg, C. Carbohydr. Res. 1980, 83, 157) by oxidative hydrolysis with NBS in aqueous acetone: Groneberg, R. D.; Miyasaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwasbuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593 (for an analogous hydrolysis procedure, see: Motavia, M. S.; Marcussen, J.; Moller, B. L. J. Carbohydr. Chem. 1995, 14, 1279).
79. Lactols 40 and 41 were easily obtained in two steps from the corresponding free sugar: Decoster, E.; Lacombe, J.-M.; Strebler, J.-L.; Ferrari, B.; Pavia, A. A. J. Carbohydr. Chem. 1983, 2, 329. Lactol 42 cannot be prepared using this methodology, and it was in turn obtained from the corresponding thiophenyl glycoside (Garegg, P. J.; Hultberg, H.; Lindberg, C. Carbohydr. Res. 1980, 83, 157) by oxidative hydrolysis with NBS in aqueous acetone: Groneberg, R. D.; Miyasaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwasbuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593 (for an analogous hydrolysis procedure, see: Motavia, M. S.; Marcussen, J.; Moller, B. L. J. Carbohydr. Chem. 1995, 14, 1279).
80. 1H NMR of the crude reaction mixture.
81. A minor cyclopentane product was also isolated in this case (see Experimental Section and the Supporting Information), but its structure could not be fully determined.
82. Tejima, S.; Ness, R. K.; Kaufman, R. L.; Fletcher, H. G. Carbohydr. Res. 1968, 7, 485.
83. 2-induced pinacol coupling for the direct transformation of alditol-derived 1,6-diols into inositol derivatives: Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898.
84. 2-induced pinacol coupling for the direct transformation of alditol-derived 1,6-diols into inositol derivatives: Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898.
85. 13c allowed a more complete analysis of the different Products formed.
86. Marco-Contelles, J.; Pozuelo, C.; Jimeno, M. L.; Martínez, L.; Martínez-Grau, A. J. Org. Chem. 1992, 57, 2625.
87. Dess, D. B.; Martin, J. C.; J. Am. Chem. Soc. 1991, 113, 7277, and references cited therein.
88. 2O and pyridine at room temperature affording the N,O-diacetylated compounds. The tertiary hydroxyl of compound 68 is unreactive under these conditions, and when the acetylation was performed in the presence of catalytic DMAP a complex mixture of products resulted.
89. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
90. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
91. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
92. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
93. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
94. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
95. 2-promoted reactions in the presence of water, see for example: (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. (b) Otsubo, K.; Inanaga, J.; Yamagushi, M. Tetrahedron Lett. 1986, 27, 5763. (c) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008. (d) Kamoshi, Y.; Kudo, T. Chem. Lett. 1993, 1495. (e) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett. 1993, 2129. (f) Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Heterocycles 1993, 36, 2383. (g) Hanessian, S.; Girard, C. Synlett 1994, 861; see also ref 19a.
96. The other minor carbocyclic products 50b-d were not isolated under these conditions.
97. 28b have recently shown that oxime ethers are not electrochemically reducible under the same conditions as they are coupled to ketones, which led them to propose a similar mechanism for the corresponding electrochemical cross-coupling.
98. (a) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
99. (b) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125.
100. 28b may suggest that the reaction of the anti-form of simple oximes is faster than that of the syn-form under electrochemical conditions.
101. See the Supporting Information.