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Volumn 70, Issue 6, 2005, Pages 2325-2328

General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ENZYME INHIBITION; OLEFINS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 15444367790     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048172s     Document Type: Article
Times cited : (132)

References (87)
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    • Gruters, R.A.1    Neefjes, J.J.2    Tersmette, M.3    Goede, R.E.Y.4    Tulp, A.5    Huisman, H.G.6    Miedema, F.7    Ploegh, H.L.8
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    • Therapeutic utility, (a) Johnston, P. S.; Lebovitz, H. E.; Coniff, R. F.; Simonson, D. C.; Raskin, P.; Munera, C. L. J. Clin. Endocrinol. Metab. 1998, 83, 1515-1522. (b) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74-76. (c) Tsuruoka, T.; Fukuyasu, H.; Ishii, M.; Usui, T.; Shibahara, S.; Inouye, S. J. Antibiot. 1996, 49, 155-161.
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    • Tsuruoka, T.1    Fukuyasu, H.2    Ishii, M.3    Usui, T.4    Shibahara, S.5    Inouye, S.6
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (2004) J. Org. Chem. , vol.69 , pp. 3565-3568
    • McDonnell, C.1    Cronin, L.2    O'Brien, J.L.3    Murphy, P.V.4
  • 19
    • 0037430461 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2387-2391
    • Singh, O.V.1    Han, H.2
  • 20
    • 0037434027 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (2003) Tetrahedron , vol.59 , pp. 281-286
    • Knight, J.G.1    Tchabanenko, K.2
  • 21
    • 0033575495 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1999) Tetrahedron , vol.55 , pp. 8931-8952
    • Meyers, A.I.1    Andres, C.J.2    Resek, J.E.3    Woodall, C.C.4    McLaughlin, M.A.5    Lee, P.H.6    Price, D.A.7
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5331-5332
    • Shirai, M.1    Okamoto, S.2    Sato, F.3
  • 23
    • 0000929876 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1998) J. Org. Chem. , vol.63 , pp. 841-859
    • Wu, X.-D.1    Khim, S.-K.2    Zhang, X.3    Cederstrom, E.M.4    Mariano, P.S.5
  • 24
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 741-746
    • Xu, Y.-M.1    Zhou, W.-S.2
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1994) J. Org. Chem. , vol.59 , pp. 3175-3185
    • Baxter, E.W.1    Reitz, A.B.2
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2621-2623
    • Park, K.H.1    Yoon, Y.J.2    Lee, S.G.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1989) Tetrahedron , vol.45 , pp. 327-336
    • Fleet, G.W.J.1    Ramsden, N.G.2    Witty, D.R.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1989) Tetrahedron , vol.45 , pp. 319-326
    • Fleet, G.W.J.1    Ramsden, N.G.2    Witty, D.R.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4645-4648
    • Pederson, R.L.1    Kim, M.-J.2    Wong, C.-H.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391. (c) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281-286. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (e) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (f) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (i) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (j) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (k) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (l) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (m) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126.
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    • Bernotas, R.C.1    Ganem, B.2
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6839-6841
    • Comins, D.L.1    Fulp, A.B.2
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7173-7176
    • Lindstrom, U.M.1    Somfai, P.2
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4989-4990
    • Berger, A.1    Ebner, M.2    Stuetz, A.E.3
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 2043-2053
    • Ermert, P.1    Vasella, A.2
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2085-2088
    • Anzeveno, P.B.1    Creemer, L.J.2
  • 36
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    • Selected synthesis of 1-deoxynojirimycin: (a) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839-6841. (b) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (b) Berger, A.; Ebner, M.; Stuetz, A. E. Tetrahedron Lett. 1995, 36, 4989-4990. (c) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043-2053. (d) Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
    • (1987) J. Org. Chem. , vol.52 , pp. 3337-3342
    • Iida, H.1    Yamazaki, N.2    Kibayashi, C.3
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    • Reviews on this subject: (a) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3712. (b) Maier, M. E. Angew. Chem., Int Ed. 2000, 39, 2073-2077. (c) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (d) Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieraugel, H. Eur. J. Org. Chem. 1999, 959-968.
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    • Felpin, F.-X.1    Lebreton, J.2
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    • (1999) Aldrichimica Acta , vol.32 , pp. 75-89
    • Phillips, A.J.1    Abell, A.D.2
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    • Pandit, U.K.1    Overkleeft, H.S.2    Borer, B.C.3    Bieraugel, H.4
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    • Wavefuction, Inc.; Irvine, CA
    • Spartan 02'; Wavefuction, Inc.; Irvine, CA.
    • Spartan 02'


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