Tandem cycloadditions of functionalized bis-dienes. An orthogonal route to new dipseudoglycals

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9348-9357

  Guillam, Anne ^a   Toupet, Loïc ^b   Maddaluno, Jacques ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

ARTICLE; CHROMATOGRAPHY; CYCLIZATION; DRUG SYNTHESIS; ENERGY CONSERVATION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TANDEM REPEAT;

EID: 0033601211     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990852l     Document Type: Article

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24. Previous examples of elimination-based diene synthesis: (a) Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. (b) Fujiwara, S.; Katsumura, S.; Isoe, S. Tetrahedron Lett. 1990, 31, 691-694. (c) Venturello, P. J. Chem. Soc. Chem. Commun. 1992, 1032-1033. (d) Mason, P. H.; Emslie, N. D. Tetrahedron, 1995, 57, 2673-2678. (e) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
25. Previous examples of elimination-based diene synthesis: (a) Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. (b) Fujiwara, S.; Katsumura, S.; Isoe, S. Tetrahedron Lett. 1990, 31, 691-694. (c) Venturello, P. J. Chem. Soc. Chem. Commun. 1992, 1032-1033. (d) Mason, P. H.; Emslie, N. D. Tetrahedron, 1995, 57, 2673-2678. (e) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
26. Previous examples of elimination-based diene synthesis: (a) Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. (b) Fujiwara, S.; Katsumura, S.; Isoe, S. Tetrahedron Lett. 1990, 31, 691-694. (c) Venturello, P. J. Chem. Soc. Chem. Commun. 1992, 1032-1033. (d) Mason, P. H.; Emslie, N. D. Tetrahedron, 1995, 57, 2673-2678. (e) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
27. Previous examples of elimination-based diene synthesis: (a) Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. (b) Fujiwara, S.; Katsumura, S.; Isoe, S. Tetrahedron Lett. 1990, 31, 691-694. (c) Venturello, P. J. Chem. Soc. Chem. Commun. 1992, 1032-1033. (d) Mason, P. H.; Emslie, N. D. Tetrahedron, 1995, 57, 2673-2678. (e) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
28. Previous examples of elimination-based diene synthesis: (a) Mioskowski, C.; Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522. (b) Fujiwara, S.; Katsumura, S.; Isoe, S. Tetrahedron Lett. 1990, 31, 691-694. (c) Venturello, P. J. Chem. Soc. Chem. Commun. 1992, 1032-1033. (d) Mason, P. H.; Emslie, N. D. Tetrahedron, 1995, 57, 2673-2678. (e) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
29. The double bond configurations of these compounds have been deduced from NMR coupling constant measurements and NOE experiments and the isomer ratios confirmed by GC and GC/MS analysis.
30. Broekhuis, A. A.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays-Bas 1980, 99, 6-12.
31. For a detailled theoretical analysis of a comparable deprotonation step, see: Fossey, J.; Ghigo, G.; Tonachini, G.; Venturello, P. Tetrahedron 1997, 53, 7937-7946.
32. 1H NMR integration) of the adduct derived from EZE′E′ isomer 3.
33. For a comparable discussion see: Lubineau, A.; Queneau, Y. J. Org. Chem. 1987, 52, 1001-1007.
34. Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem., 1998, 63, 5110-5122.
35. 3 to the eluant induces a quantitative aromatization of 7 into phthalimide.
36. Mellor, J. M.; Webb, C. F. J. Chem. Soc., Perkin Trans. 2 1974, 17-22.
37. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
38. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
39. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
40. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
41. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
42. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935-938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
43. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741-760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
44. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
45. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
46. See inter alia: (a) Banaszek, A. Bull. Acad. Polon. Sci. Ser. Sci. Chim. 1974, 22, 1045-1051. (b) Angerbauer, R.; Schmidt, R. R. Carbohydr. Res. 1981, 89, 193-201. (c) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259. (d) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Eng. 1987, 26, 15-23. (e) Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1990, 1178-1179. (f) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935- 938. (g) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741- 760. (h) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Eng. 1996, 35, 1380-1419. (i) Kleindl, P. J.; Donaldson, W. A. J. Org. Chem. 1997, 62, 4176-4179. (j) Seeberger, P. H.; Bilodeau, M. T.; Danishefsky, S. J. Aldrichim. Acta 1997, 30, 75-92.
47. See inter alia: (a) Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415-424. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem., Int. Ed. Eng. 1994, 33, 980-982. (c) Dondoni, A.; Kniezo, L.; Martinkova, M. J. Chem. Soc. Chem. Commun. 1994, 1963-1964. (d) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007-4010.
48. See inter alia: (a) Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415-424. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem., Int. Ed. Eng. 1994, 33, 980-982. (c) Dondoni, A.; Kniezo, L.; Martinkova, M. J. Chem. Soc. Chem. Commun. 1994, 1963-1964. (d) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007-4010.
49. See inter alia: (a) Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415-424. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem., Int. Ed. Eng. 1994, 33, 980-982. (c) Dondoni, A.; Kniezo, L.; Martinkova, M. J. Chem. Soc. Chem. Commun. 1994, 1963-1964. (d) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007-4010.
50. See inter alia: (a) Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415-424. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem., Int. Ed. Eng. 1994, 33, 980-982. (c) Dondoni, A.; Kniezo, L.; Martinkova, M. J. Chem. Soc. Chem. Commun. 1994, 1963-1964. (d) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007-4010.
51. Several di- and trisaccharides have been prepared through a single heterocycloaddition step involving sugar-bound dienes: (a) David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274-2278. (b) David, S.; Lubineau, A.; Thieffry, A. Tetrahedron 1978, 34, 299-304. (c) David, S.; Lubineau, A.; Vatèle, J. J. Chem. Soc. Chem. Commun. 1978, 535-537. (d) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230-2234. (e) Larsen, D. E.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
52. Several di- and trisaccharides have been prepared through a single heterocycloaddition step involving sugar-bound dienes: (a) David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274-2278. (b) David, S.; Lubineau, A.; Thieffry, A. Tetrahedron 1978, 34, 299-304. (c) David, S.; Lubineau, A.; Vatèle, J. J. Chem. Soc. Chem. Commun. 1978, 535-537. (d) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230-2234. (e) Larsen, D. E.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
53. Several di- and trisaccharides have been prepared through a single heterocycloaddition step involving sugar-bound dienes: (a) David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274-2278. (b) David, S.; Lubineau, A.; Thieffry, A. Tetrahedron 1978, 34, 299-304. (c) David, S.; Lubineau, A.; Vatèle, J. J. Chem. Soc. Chem. Commun. 1978, 535-537. (d) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230-2234. (e) Larsen, D. E.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
54. Several di- and trisaccharides have been prepared through a single heterocycloaddition step involving sugar-bound dienes: (a) David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274-2278. (b) David, S.; Lubineau, A.; Thieffry, A. Tetrahedron 1978, 34, 299-304. (c) David, S.; Lubineau, A.; Vatèle, J. J. Chem. Soc. Chem. Commun. 1978, 535-537. (d) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230-2234. (e) Larsen, D. E.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
55. Several di- and trisaccharides have been prepared through a single heterocycloaddition step involving sugar-bound dienes: (a) David, S.; Eustache, J.; Lubineau, A. J. Chem. Soc., Perkin Trans. 1 1974, 2274-2278. (b) David, S.; Lubineau, A.; Thieffry, A. Tetrahedron 1978, 34, 299-304. (c) David, S.; Lubineau, A.; Vatèle, J. J. Chem. Soc. Chem. Commun. 1978, 535-537. (d) David, S.; Eustache, J. J. Chem. Soc., Perkin Trans. 1 1979, 2230-2234. (e) Larsen, D. E.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
56. In absence of any anomeric linkage, the compounds derived from 12a/12b cannot be considered as disaccharides.
57. Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. 1969, 587-591.
58. Thiem, J.; Schwenter, J.; Schüttpelz, E.; Kopf, J. Chem. Ber. 1979, 112, 1023-1034.
59. 13C NMR spectrum of 17. The diastereoselectivity of this step is therefore to be considered as uncertain.
60. These measures of relatively small coupling constants have to be done while decoupling the vinylic methyl group to simplify the signals of interest. The values obtained for these constants are in agreement with published data on comparable systems; see for instance: (a) Achmatowicz, O.; Bukowski, P. Rocz. Chem. 1973, 47, 99-113. (b) Dawe, R. D.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 522- 528. (c) Takeda, K.; Nakamura, H.; Ayabe, A.; Akiyama, A.; Harigaya, Y.; Mizuno, Y. Tetrahedron Lett. 1994, 35, 125-128.
61. These measures of relatively small coupling constants have to be done while decoupling the vinylic methyl group to simplify the signals of interest. The values obtained for these constants are in agreement with published data on comparable systems; see for instance: (a) Achmatowicz, O.; Bukowski, P. Rocz. Chem. 1973, 47, 99-113. (b) Dawe, R. D.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 522-528. (c) Takeda, K.; Nakamura, H.; Ayabe, A.; Akiyama, A.; Harigaya, Y.; Mizuno, Y. Tetrahedron Lett. 1994, 35, 125-128.
62. These measures of relatively small coupling constants have to be done while decoupling the vinylic methyl group to simplify the signals of interest. The values obtained for these constants are in agreement with published data on comparable systems; see for instance: (a) Achmatowicz, O.; Bukowski, P. Rocz. Chem. 1973, 47, 99-113. (b) Dawe, R. D.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 522- 528. (c) Takeda, K.; Nakamura, H.; Ayabe, A.; Akiyama, A.; Harigaya, Y.; Mizuno, Y. Tetrahedron Lett. 1994, 35, 125-128.
63. (a) Ekelöf, K.; Garegg, P. J.; Olsson, L.; Oscarson, S. Pure Appl. Chem. 1997, 69, 1847-1852.
64. (b) Kassab, D. J.; Ganem, B. J. Org. Chem. 1899, 64, 1782-1783.
65. Review on pseudosugars: (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283. (b) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162. Among recent results, see: (c) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 51, 8841-8844. (d) Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 51, 8845-8848. (e) Sudha, A. V. R. L.; Nagarajan, M. J. Chem. Soc. Chem. Commun. 1998, 925-926.
66. Review on pseudosugars: (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283. (b) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162. Among recent results, see: (c) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 51, 8841-8844. (d) Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 51, 8845-8848. (e) Sudha, A. V. R. L.; Nagarajan, M. J. Chem. Soc. Chem. Commun. 1998, 925-926.
67. Review on pseudosugars: (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283. (b) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162. Among recent results, see: (c) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 51, 8841-8844. (d) Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 51, 8845-8848. (e) Sudha, A. V. R. L.; Nagarajan, M. J. Chem. Soc. Chem. Commun. 1998, 925-926.
68. Review on pseudosugars: (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283. (b) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162. Among recent results, see: (c) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 51, 8841-8844. (d) Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 51, 8845-8848. (e) Sudha, A. V. R. L.; Nagarajan, M. J. Chem. Soc. Chem. Commun. 1998, 925-926.
69. Review on pseudosugars: (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283. (b) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162. Among recent results, see: (c) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 51, 8841-8844. (d) Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 51, 8845-8848. (e) Sudha, A. V. R. L.; Nagarajan, M. J. Chem. Soc. Chem. Commun. 1998, 925-926.
70. Recent results on pseudodisaccharides: (a) Lallemand, M. C.; Desjardins, M.; Freeman, S.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 7693-7696. (b) Tagmose, T. M.; Bols, M. Chem. Eur. J. 1997, 3, 453- 462. (c) Ogawa, S.; Hirai, K.; Odagiri, T.; Matsunaga, T.; Yamazaki, T.; Nakajima, A. Eur. J. Org. Chem. 1998, 1099, 9-1109. (d) Haines, A. H.; Carvalho, I. J. Chem. Soc. Chem. Commun. 1998, 817-818.
71. Recent results on pseudodisaccharides: (a) Lallemand, M. C.; Desjardins, M.; Freeman, S.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 7693-7696. (b) Tagmose, T. M.; Bols, M. Chem. Eur. J. 1997, 3, 453-462. (c) Ogawa, S.; Hirai, K.; Odagiri, T.; Matsunaga, T.; Yamazaki, T.; Nakajima, A. Eur. J. Org. Chem. 1998, 1099, 9-1109. (d) Haines, A. H.; Carvalho, I. J. Chem. Soc. Chem. Commun. 1998, 817-818.
72. Recent results on pseudodisaccharides: (a) Lallemand, M. C.; Desjardins, M.; Freeman, S.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 7693-7696. (b) Tagmose, T. M.; Bols, M. Chem. Eur. J. 1997, 3, 453- 462. (c) Ogawa, S.; Hirai, K.; Odagiri, T.; Matsunaga, T.; Yamazaki, T.; Nakajima, A. Eur. J. Org. Chem. 1998, 1099, 9-1109. (d) Haines, A. H.; Carvalho, I. J. Chem. Soc. Chem. Commun. 1998, 817-818.
73. Recent results on pseudodisaccharides: (a) Lallemand, M. C.; Desjardins, M.; Freeman, S.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 7693-7696. (b) Tagmose, T. M.; Bols, M. Chem. Eur. J. 1997, 3, 453- 462. (c) Ogawa, S.; Hirai, K.; Odagiri, T.; Matsunaga, T.; Yamazaki, T.; Nakajima, A. Eur. J. Org. Chem. 1998, 1099, 9-1109. (d) Haines, A. H.; Carvalho, I. J. Chem. Soc. Chem. Commun. 1998, 817-818.