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Volumn 62, Issue 7, 1997, Pages 1916-1917

Protecting group-directed, diastereoselective samarium diiodide-promoted carbocyclization: Application to the synthesis of cyclitols

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; POLYOL;

EID: 0030945610     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9623898     Document Type: Article
Times cited : (27)

References (42)
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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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 13
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    • 7a and 7b were prepared in five and four steps, respectively, from D-mannitol. See the Supporting Information.
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    • All new compounds showed correct microanalytical and spectroscopic data
    • All new compounds showed correct microanalytical and spectroscopic data.
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    • For an application of this methodology cyclitols, see ref 13e
    • 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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    • See ref 18a. For other syntheses of conduritol E, see: Angelaud, R.; Landais, Y. J. Org. Chem. 1996, 61, 5202-5203 and references cited therein.
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