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Volumn , Issue 10, 2003, Pages 1521-1523

A practical access to [1-13c]1-deoxy-d-xylulose and its derivatives

Author keywords

Biosynthesis; Carbohydrates; Isotope; Labeled compound; Natural products; Stereoselective synthesis; Terpenoids

Indexed keywords

XYLULOSE;

EID: 0042697199     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40860     Document Type: Article
Times cited : (9)

References (22)
  • 3
    • 0037064471 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8265
    • Querol, J.1    Grosdemange-Billiard, C.2    Rohmer, M.3    Boronat, A.4    Imperial, S.5
  • 4
    • 0035356040 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (2001) J. Org. Chem. , vol.66 , pp. 3948
    • Hecht, S.1    Kis, K.2    Eisenreich, W.3    Amslinger, S.4    Wungsintaweekul, J.5    Herz, S.6    Rohdich, F.7    Bacher, A.8
  • 5
    • 0033582687 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1437
    • Shabat, D.1    List, B.2    Lerner, R.A.3    Barbas C.F. III4
  • 6
    • 0035649382 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (2001) J. Carbohydr. Chem. , vol.20 , pp. 833
    • Fechter, M.H.1    Gaisberger, R.2    Griengl, H.3
  • 7
    • 0035969620 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (2001) Org. Lett. , vol.3 , pp. 3819
    • Zhao, S.1    Petrus, L.2    Serianni, A.S.3
  • 8
    • 0035938378 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3065
    • Hoeffler, J.-F.1    Grosdemange-Billiard, C.2    Rohmer, M.3
  • 9
    • 0033525674 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1999) J. Org. Chem. , vol.64 , pp. 1508
    • Blagg, B.S.1    Poulter, C.D.2
  • 10
    • 0033578624 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6913
    • Jux, A.1    Boland, W.2
  • 11
    • 0033575418 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5307
    • Thiel, R.1    Adam, K.P.2
  • 12
    • 0000188835 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1998) J. Org. Chem. , vol.63 , pp. 2375
    • Tayler, S.V.1    Vu, L.D.2    Begley, T.P.3
  • 13
    • 0032559979 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2479
    • Giner, J.-L.1
  • 14
    • 0030863368 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6387
    • Piel, J.1    Boland, W.2
  • 15
    • 0031003397 scopus 로고    scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1997) Z. Naturforsch., C: Biosci. , vol.52 , pp. 15
    • Zeidler, J.G.1    Lichtenthaler, H.K.2    May, H.U.3    Lichtenthaler, F.W.4
  • 16
    • 0000185613 scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1995) Can. J. Chem. , vol.73 , pp. 1329
    • Kennedy, I.A.1    Hemscheidt, T.2    Britten, J.F.3    Spenser, I.D.4
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    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1995) J. Carbohydr. Chem. , vol.14 , pp. 171
    • Backstrom, A.D.1    McMordie, R.A.S.2    Begley, T.P.3
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    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2131
    • David, S.1    Estramareix, B.2    Fischer, J.-C.3    Therisod, M.4
  • 19
    • 33947489704 scopus 로고
    • For the enzymatic synthesis, see: (a) Querol, J.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A.; Imperial, S. Tetrahedron Lett. 2002, 43, 8265. (b) Hecht, S.; Kis, K.; Eisenreich, W.; Amslinger, S.; Wungsintaweekul, J.; Herz, S.; Rohdich, F.; Bacher, A. J. Org. Chem. 2001, 66, 3948. (c) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F. III. Tetrahedron Lett. 1999, 40, 1437. (d) For the chemical synthesis, see: Fechter, M. H.; Gaisberger, R.; Griengl, H. J. Carbohydr. Chem. 2001, 20, 833. (e) Zhao, S.; Petrus, L.; Serianni, A. S. Org. Lett. 2001, 3, 3819. (f) See also: Hoeffler, J.-F.; Grosdemange-Billiard, C.; Rohmer, M. Tetrahedron Lett. 2001, 42, 3065. (g) Blagg, B. S.; Poulter, C. D. J. Org. Chem. 1999, 64, 1508. (h) See further: Jux, A.; Boland, W. Tetrahedron Lett. 1999, 40, 6913. (i) Thiel, R.; Adam, K. P. Tetrahedron Lett. 1999, 40, 5307. (j) Tayler, S. V.; Vu, L. D.; Begley, T. P. J. Org. Chem. 1998, 63, 2375. (k) Giner, J.-L. Tetrahedron Lett. 1998, 39, 2479. (1) Piel, J.; Boland, W. Tetrahedron Lett. 1997, 38, 6387. (m) Zeidler, J. G.; Lichtenthaler, H. K.; May, H. U.; Lichtenthaler, F. W. Z. Naturforsch., C: Biosci. 1997, 52, 15. (n) Kennedy, I. A.; Hemscheidt, T.; Britten, J. F.; Spenser, I. D. Can. J. Chem. 1995, 73, 1329. (o) Backstrom, A. D.; McMordie, R. A. S.; Begley, T. P. J. Carbohydr. Chem. 1995, 14, 171. (p) David, S.; Estramareix, B.; Fischer, J.-C.; Therisod, M. J. Chem. Soc., Perkin Trans. 1 1982, 2131. (q) For the synthesis of 1-deoxy-L-xylulose, see tribenzoate: Wolfrom, M. L.; Bennet, R. B. J. Org. Chem. 1965, 30, 458.
    • (1965) J. Org. Chem. , vol.30 , pp. 458
    • Wolfrom, M.L.1    Bennet, R.B.2
  • 22
    • 0042566347 scopus 로고    scopus 로고
    • note
    • 31P NMR: δ = -6.4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.