An approach to the bicyclic core of the zaragozic acids via the aldol reaction between methyl (α-D-xylofuranoside)uronate and D-(R)-glyceraldehyde acetonide

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11819-11832

  Fraisse, Pierre ^a   Hanna, Issam ^a   Lallemand, Jean Yves ^a   Prangé, Thierry ^b   Ricard, Louis ^c  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b CNRS   (France)

^c LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

(R) glyceraldehyde acetonide; Aldol reaction; Zaragozic Acids; D xylofuranuronic acid

Indexed keywords

GLYCERALDEHYDE; NATURAL PRODUCT; ZARAGOZIC ACID A; ZARAGOZIC ACID C;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033214434     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00637-7     Document Type: Article

References (53)

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36. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
37. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
38. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
39. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
40. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
41. 3 see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett., 1984, 25, 4233-4236. Imamoto, T.; Kusumoto, T.; Yokoyama, M. Tetrahedron Lett., 1983, 24, 5233-5236. Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett., 1985, 26, 6477-6480. Al-Said, N. H.; Liu, H.-J. Tetrahedron Lett., 1991, 32, 5473. Shang, X.; Liu, H.-J. Synth. Commun., 1995, 25, 2155-2159. Bartoli, G.; Bosco, M.;Van Beek, J.; Sambri, L.; Marcantoni, E.Tetrahedron Lett., 1996, 37, 2293-2296.
42. A small amount of THF must be added in order to prevent solidification of the reaction mixture at -100·C. Nevertheless, performing the reaction in a non-coordinating solvent such as toluene was found to greatly improve both the yield and the reproducibility. For a similar observation, see: D. Alker, D. Neville Jones, G. M. Taylor, W. W. Wood, Tetrahedron Lett. 1991, 32, 1667-1670.
43. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
44. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
45. 2 led to a 95:5 mixture of ketoesters 6 albeit in a lower yield and with poor reproducibility.
46. 1 = 0.0408, G.O.F. = 1.077.
47. 1 = 0.0845, G.O.F. = 1.07.
48. For a review see: David, S.; Hanessian, S. Tetrahedron, 1985, 41, 643-663.
49. See for examples: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem., 1995, 60, 2780-2785. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340.
50. See for examples: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem., 1995, 60, 2780-2785. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340.
51. See for examples: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem., 1995, 60, 2780-2785. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340.
52. See for examples: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem., 1995, 60, 2780-2785. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340.
53. See for examples: Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem., 1995, 60, 2780-2785. Paterson, I.; Feßner, K.; Finaly, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117-1120. Hegde, S. G.; Myles, D. C. Tetrahedron 1997, 53, 11179-11190. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340.