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8244243282
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note
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2
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5
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0028936033
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For other recent approaches to the synthesis of hydrolytically stable analogs, see, for example: (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169. (b) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (c) Eisele, T.; Toepfer, A.; Kretzscmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389-1392. (d) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803.
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Jun, H.-S.4
Haudrechy-Bretel, N.5
Kishi, Y.6
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6
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0030062615
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For other recent approaches to the synthesis of hydrolytically stable analogs, see, for example: (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169. (b) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (c) Eisele, T.; Toepfer, A.; Kretzscmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389-1392. (d) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803.
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Aguilera, B.1
Fernández-Mayoralas, A.2
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7
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0029988587
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For other recent approaches to the synthesis of hydrolytically stable analogs, see, for example: (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169. (b) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (c) Eisele, T.; Toepfer, A.; Kretzscmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389-1392. (d) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803.
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Eisele, T.1
Toepfer, A.2
Kretzscmar, G.3
Schmidt, R.R.4
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8
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0029860709
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For other recent approaches to the synthesis of hydrolytically stable analogs, see, for example: (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169. (b) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (c) Eisele, T.; Toepfer, A.; Kretzscmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389-1392. (d) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803.
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Jiménez-Barbero, J.6
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Abad-Rodríguez, J.8
Nieto-Sampedro, M.9
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0026801605
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0029846624
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Espinosa, J.-F.; Cañada, F. J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862-10871.
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The conformational study of pseudodisaccharides bearing a carbaaugar in the reducing end has been reported: Duus, J. Ø.; Bock, K.; Ogawa, S. Carbohydr. Res. 1994, 252, 1-18.
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19
-
-
8244249527
-
-
note
-
2) at both sides of the molecule. A further simplification of the synthesis could be imagined if the olefin and trans-diol functional groups in 5 and ent-5 were interconvertible with each other, defining then a latent plane of symmetry that would make possible the use of any of these compounds as a more advanced intermediate in the synthesis. Efforts in this direction will be addressed in the near future.
-
-
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20
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2142715741
-
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For recent reviews on applications of samarium diiodide in organic synthesis, see: Molander, G. A. Chem. Rev. 1996, 96, 307-338.
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For samarium diiodide-promoted pinacol coupling of related carbohydrate derivatives, see: (a) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. (b) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671-6672. (c) Chiara, J. L., Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898. (d) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885-886.
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Chiara, J.L.1
Martín-Lomas, M.2
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0028106715
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For samarium diiodide-promoted pinacol coupling of related carbohydrate derivatives, see: (a) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. (b) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671-6672. (c) Chiara, J. L., Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898. (d) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885-886.
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Guidot, J.P.1
Le Gall, T.2
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23
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0029149758
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For samarium diiodide-promoted pinacol coupling of related carbohydrate derivatives, see: (a) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. (b) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671-6672. (c) Chiara, J. L., Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898. (d) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885-886.
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Chiara, J.L.1
Valle, N.2
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24
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0030049755
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For samarium diiodide-promoted pinacol coupling of related carbohydrate derivatives, see: (a) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. (b) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671-6672. (c) Chiara, J. L., Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895-1898. (d) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885-886.
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0001692942
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13 although the opposite stereochemistry has been observed in acyclic systems: Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. See also: Rang, M.; Park, J.; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1996, 61, 5528-5531.
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0029784980
-
-
13 although the opposite stereochemistry has been observed in acyclic systems: Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. See also: Rang, M.; Park, J.; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1996, 61, 5528-5531.
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8244238438
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note
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13
-
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28
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8244220396
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note
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7a and 7b were prepared in five and four steps, respectively, from D-mannitol. See the Supporting Information.
-
-
-
-
29
-
-
8244223225
-
-
All new compounds showed correct microanalytical and spectroscopic data
-
All new compounds showed correct microanalytical and spectroscopic data.
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30
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84987579084
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For other syntheses of neo- and allo-inositol, see: (b) Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives. A Handbook of Physical, Spectral and Synthetic Data; VCH Publishers: New York, 1993. (c) Hudlicky, T.; Mandel, M.; Rouden, J.; Lee, R. S.; Bachmann, B.; Dudding, T.; Yost, K. J.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1994, 1553-1567 and references cited therein.
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For other syntheses of neo- and allo-inositol, see: (b) Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives. A Handbook of Physical, Spectral and Synthetic Data; VCH Publishers: New York, 1993. (c) Hudlicky, T.; Mandel, M.; Rouden, J.; Lee, R. S.; Bachmann, B.; Dudding, T.; Yost, K. J.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1994, 1553-1567 and references cited therein.
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33947483562
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For an application of this methodology cyclitols, see ref 13e
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Corey, E. J.; Winter, R. A. E. J. Am. Chem. Soc. 1963, 85, 2677-2678. For an application of this methodology cyclitols, see ref 13e.
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