Applications of Sugar Nitrones in Synthesis: The Total Synthesis of (+)-Polyoxin J

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5497-5507

  Dondoni, Alessandro ^a,b   Franco, Santiago ^a   Junquera, Federico ^b   Merchán, Francisco L ^b   Merino, Pedro ^b   Tejero, Tomás ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000918830     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702913     Document Type: Article

References (76)

1. A preliminary account of this work has been published: Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. J. Chem. Soc., Chem. Commun. 1995, 2127.
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3. (a) Isolation: Suzuki, S.; Isono, K.; Nagatsu, J.; Mizutani, T.; Kawashima, Y.; Mizuno, T. J. Antibiot., Ser. A. 1965, 18, 131. Isono, K.; Kobinata, K.; Suzuki, S. Agr. Biol. Chem. 1968, 32, 792.
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5. (c) Reviews: Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333. Isono, K. J. Antibiot. 1988, 41, 1711.
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7. A stereochemical revision (cis instead of trans) of the 3-ethylidene-L-azetine-2-carboxilic acid (polyoximic acid) that is present in this compound has been recently reported. See: Hanessian, S.; Fu, J.-M.; Tu, Y.; Isono, K. Tetrahedron Lett. 1993, 34, 4153.
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14. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
15. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
16. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
17. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
18. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
19. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A. S.; Naider, F. J. Med. Chem. 1983, 26, 1518. Emmer, G.; Ryder, N. S.; Grassberger, M. A. J. Med. Chem. 1985, 28, 278. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307. Fiandor, J.; Garcia-López, M.-T.; De las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1987, 978. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174. Cooper, A. B.; Desai, J. Lovey, R. G.; Saksena, A. K.; Girijavallabhan, V. M.; Ganguly, A. K.; Loebenberg, D.; Parmegiani, R.; Cacciapuoti, A. Bioorg. Med. Chem. Lett. 1993, 3, 1079.
20. For a review on this topic, see: Saksena, A. K.; Girijavallabhan, V. M.; Cooper, B.; Loebenberg, D. Annu. Rep. Med. Chem. 1989, 24, 111.
21. Kuzuhara, H.; Ohrui, H.; Emoto, S. Tetrahedron Lett. 1973, 5055.
22. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111.
23. For early syntheses of polyoxamic acid derivatives and the nucleoside portions of polyoxins, see: Garner, P. Studies in Natural Products Chemistry. Vol. 1. Stereoselective Synthesis. Part A; Atta-Ur Rahman, Ed., Elsevier: Amsterdam, 1988; p 397.
24. Recent syntheses of polyoxamic acid derivatives: (a) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (b) Duréault, A.; Carreaux, F.; Depezay, J. C. Tetrahedron Lett. 1989, 30, 4527. (c) Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265. (d) Banik, B. K. Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307.
25. Recent syntheses of polyoxamic acid derivatives: (a) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (b) Duréault, A.; Carreaux, F.; Depezay, J. C. Tetrahedron Lett. 1989, 30, 4527. (c) Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265. (d) Banik, B. K. Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307.
26. Recent syntheses of polyoxamic acid derivatives: (a) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (b) Duréault, A.; Carreaux, F.; Depezay, J. C. Tetrahedron Lett. 1989, 30, 4527. (c) Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265. (d) Banik, B. K. Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307.
27. Recent syntheses of polyoxamic acid derivatives: (a) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (b) Duréault, A.; Carreaux, F.; Depezay, J. C. Tetrahedron Lett. 1989, 30, 4527. (c) Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265. (d) Banik, B. K. Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307.
28. (e) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990.
29. (f) Matsumura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733.
30. (g) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139
31. (h) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431.
32. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
33. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
34. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
35. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
36. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
37. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
38. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
39. Recent syntheses of ribofuranosyl α-amino acid nucleosides (polyoxins C): (a) ref 11b; (b) ref 11h. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. (d) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853. (e) Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019. (f) Chen, A.; Savagen, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769. (g) Evina, C. M.; Guillerm, G. Tetrahedron Lett. 1996, 37, 163. (h) Ohrui, H.; Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1971, 4267.
40. Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520.
41. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450.
42. Dondoni, A.; Junquera, F.; Merchán F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T., accompanying paper.
43. Dondoni, A.; Franco S.; Junquera, F.; Merchán F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537.
44. Synthesis of 5-O-carbamoylpolyoxamic acid: Dondoni, A.; Franco S.; Merchán F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
45. Synthesis of thymine polyoxin C: Dondoni, A.; Junquera, F.; Merchán F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1994, 35, 9439.
46. Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265.
47. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
48. 2AlCl precomplexed nitrone 5a leads to the anti isomer of 9a (lyxo configuration) with 90% diastereoselectivity.
49. For earlier examples of the use of furan as precursor to carboxylic acid, see: (a) Mukaiyama, T.; Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. (c) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346. (d) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323. (e) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1993, 58, 6229.
50. For earlier examples of the use of furan as precursor to carboxylic acid, see: (a) Mukaiyama, T.; Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. (c) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346. (d) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323. (e) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1993, 58, 6229.
51. For earlier examples of the use of furan as precursor to carboxylic acid, see: (a) Mukaiyama, T.; Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. (c) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346. (d) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323. (e) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1993, 58, 6229.
52. For earlier examples of the use of furan as precursor to carboxylic acid, see: (a) Mukaiyama, T.; Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. (c) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346. (d) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323. (e) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1993, 58, 6229.
53. For earlier examples of the use of furan as precursor to carboxylic acid, see: (a) Mukaiyama, T.; Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. (c) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346. (d) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323. (e) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1993, 58, 6229.
54. It is worth mentioning that this problem does not exist in the exploitation of the thiazole-formyl group equivalence since the cleavage of the thiazole ring involves almost neutral and nonoxidizing reaction conditions. Aldehydes obtained by the thiazole-based method can be converted into carboxylic acids under mild oxidizing conditions. Both the unmasking of the aldehyde and the oxidation to carboxylic acid are tolerant to a wide range of functional and protecting groups. See for instance: (a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162. (b) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324. (c) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. (d) Dondoni, A.; Marra, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
55. It is worth mentioning that this problem does not exist in the exploitation of the thiazole-formyl group equivalence since the cleavage of the thiazole ring involves almost neutral and nonoxidizing reaction conditions. Aldehydes obtained by the thiazole-based method can be converted into carboxylic acids under mild oxidizing conditions. Both the unmasking of the aldehyde and the oxidation to carboxylic acid are tolerant to a wide range of functional and protecting groups. See for instance: (a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162. (b) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324. (c) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. (d) Dondoni, A.; Marra, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
56. It is worth mentioning that this problem does not exist in the exploitation of the thiazole-formyl group equivalence since the cleavage of the thiazole ring involves almost neutral and nonoxidizing reaction conditions. Aldehydes obtained by the thiazole-based method can be converted into carboxylic acids under mild oxidizing conditions. Both the unmasking of the aldehyde and the oxidation to carboxylic acid are tolerant to a wide range of functional and protecting groups. See for instance: (a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162. (b) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324. (c) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. (d) Dondoni, A.; Marra, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
57. It is worth mentioning that this problem does not exist in the exploitation of the thiazole-formyl group equivalence since the cleavage of the thiazole ring involves almost neutral and nonoxidizing reaction conditions. Aldehydes obtained by the thiazole-based method can be converted into carboxylic acids under mild oxidizing conditions. Both the unmasking of the aldehyde and the oxidation to carboxylic acid are tolerant to a wide range of functional and protecting groups. See for instance: (a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162. (b) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324. (c) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. (d) Dondoni, A.; Marra, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
58. Although we have reported the stereoselective thiazole-based homologation of aldehydes through their nitrones (Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P. Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505), this synthetic approach to 3 was excluded by the moderate syn-selectivity (ds 70%) and low yield of isolated adducts (76%) in the reaction of 2-lithiothiazole with the nitrone 5a.
59. Carlsen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
60. The authors have deposited atomic coordinates and bond lengths and angles for structure 3a with the Cambridge Crystallographic Data Centre. The data can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
61. This was kindly provided by Dr. A. K. Saksena and Dr. R. G. Lovey (Schering-Plough Research Institute, Kenilworth, NJ).
62. It has been pointed pointed out (ref 12d) that in the nucleophilic additions to aldehydes of dialdose derivatives, modest to good diastereoselectivity has been achieved only in the case where Lewis acid catalysts or chelation control have been employed. Hence it is worth recalling here that an exception to this behavior is the addition of the organometal 2-(trimethylsilyl)thiazole to dialdoses wherein high levels of nonchelation-controlled diastereoselectivity (ds ≥ 95%) were registered. See: Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. Tetrahedron 1987, 43, 3533. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693. One of us (A.D.) thanks Professor A. G. M. Barrett for the correspondence on this matter.
63. It has been pointed pointed out (ref 12d) that in the nucleophilic additions to aldehydes of dialdose derivatives, modest to good diastereoselectivity has been achieved only in the case where Lewis acid catalysts or chelation control have been employed. Hence it is worth recalling here that an exception to this behavior is the addition of the organometal 2-(trimethylsilyl)thiazole to dialdoses wherein high levels of nonchelation-controlled diastereoselectivity (ds ≥ 95%) were registered. See: Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. Tetrahedron 1987, 43, 3533. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693. One of us (A.D.) thanks Professor A. G. M. Barrett for the correspondence on this matter.
64. The reference for the preparation of the dialdose 11 has been misreported in our paper quoted in ref 16. The procedure adopted is that given in ref 12d.
65. Details of this reaction sequence as well as the characteristics of compounds 12a, 13, and 14 are reported in the Experimental Section for convenience.
66. (a) Niedbala, U.; Vorbrüggen, H. J. Org. Chem. 1974, 39, 3654.
67. (b) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
68. Hann, R. M.; Hudson, C. S. J. Am. Chem. Soc. 1934, 56, 2465.
69. For an earlier report of this procedure, see ref 18.
70. Dhavale, D. D.; Gentilucci, L.; Piazza, M. G.; Trombini, C. Liebigs Ann. Chem. 1992, 1289.
71. It is worth mentioning that while the benzyl group is removed by hydrogenolysis, the p-methoxy derivative is removed under oxidative conditions using cerium ammonium nitrate. See: Yoshimura, J.; Yamaura, M.; Suzuki, T.; Hashimoto, H.; Okamoto, T. Bull. Chem. Soc. Jpn. 1985, 58, 1413.
72. Pyrimidine nucleosides have been reported to be unstable under oxidative conditions by ruthenium(IV). See: Singh, A. K.; Varma, R. S. Tetrahedron Lett. 1992, 33, 2307.
73. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174.
74. Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sensitive Compounds; 2nd ed.; Wiley-Interscience: New York, 1986.
75. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.
76. Nishimura, T.; Iwai, I. Chem. Pharm. Bull. 1964, 12, 352.