Novel conformationally locked inositols: From aromatics to annulated cyclitols

Chemistry - A European Journal

Volumn 9, Issue 10, 2003, Pages 2264-2272

  Mehta, Goverdhan ^a   Senaiar, Ramesh S ^a   Bera, Mrinal K ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Annulation; Conformation analysis; Cyclitols; Dihydroxylation; Signal transduction

Indexed keywords

AROMATIC HYDROCARBONS; CONFORMATIONS; DERIVATIVES; SYNTHESIS (CHEMICAL);

AROMATIC PRECURSORS;

ALCOHOLS;

AROMATIC COMPOUND; INDAN DERIVATIVE; INOSITOL; TETRALIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; SIGNAL TRANSDUCTION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

INDANS; INOSITOL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; TETRAHYDRONAPHTHALENES;

EID: 0037833505     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204650     Document Type: Article

References (52)

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13. For selected references on inositol analogues, see: a) A. M. Riley, B. V. L. Potter, J. Org. Chem. 1995, 60, 4970; b) C. Liu, B. V. L. Potter, J. Org. Chem. 1997, 62, 8335; c) A. M. Riley, B. V. L. Potter, Tetrahedron Lett. 1999, 40, 2213; d) H. Sun, G. B. Reddy, C. George, E. J. Meuillet, M. Berggren, G. Powis, A. P. Kozikowski, Tetrahedron Lett. 2002, 43, 2835; e) D. J. Jenkins, A. M. Riley, B. V. L. Potter, J. Org. Chem. 1996, 61, 7719; f) A. P. Kozikowski, A. H. Fauq, G. Powis, D. C. Melder, J. Am. Chem. Soc. 1990, 112, 4528; g) A. B. Cheikh, L. E. Craine, J. Zemlicka, M. H. Heeg, Carbohydr. Res. 1990, 199, 19; h) A. Schnaars, C. Schultz, Tetrahderon 2001, 57, 519.
14. For selected references on inositol analogues, see: a) A. M. Riley, B. V. L. Potter, J. Org. Chem. 1995, 60, 4970; b) C. Liu, B. V. L. Potter, J. Org. Chem. 1997, 62, 8335; c) A. M. Riley, B. V. L. Potter, Tetrahedron Lett. 1999, 40, 2213; d) H. Sun, G. B. Reddy, C. George, E. J. Meuillet, M. Berggren, G. Powis, A. P. Kozikowski, Tetrahedron Lett. 2002, 43, 2835; e) D. J. Jenkins, A. M. Riley, B. V. L. Potter, J. Org. Chem. 1996, 61, 7719; f) A. P. Kozikowski, A. H. Fauq, G. Powis, D. C. Melder, J. Am. Chem. Soc. 1990, 112, 4528; g) A. B. Cheikh, L. E. Craine, J. Zemlicka, M. H. Heeg, Carbohydr. Res. 1990, 199, 19; h) A. Schnaars, C. Schultz, Tetrahderon 2001, 57, 519.
15. For selected references on inositol analogues, see: a) A. M. Riley, B. V. L. Potter, J. Org. Chem. 1995, 60, 4970; b) C. Liu, B. V. L. Potter, J. Org. Chem. 1997, 62, 8335; c) A. M. Riley, B. V. L. Potter, Tetrahedron Lett. 1999, 40, 2213; d) H. Sun, G. B. Reddy, C. George, E. J. Meuillet, M. Berggren, G. Powis, A. P. Kozikowski, Tetrahedron Lett. 2002, 43, 2835; e) D. J. Jenkins, A. M. Riley, B. V. L. Potter, J. Org. Chem. 1996, 61, 7719; f) A. P. Kozikowski, A. H. Fauq, G. Powis, D. C. Melder, J. Am. Chem. Soc. 1990, 112, 4528; g) A. B. Cheikh, L. E. Craine, J. Zemlicka, M. H. Heeg, Carbohydr. Res. 1990, 199, 19; h) A. Schnaars, C. Schultz, Tetrahderon 2001, 57, 519.
16. For selected references on inositol analogues, see: a) A. M. Riley, B. V. L. Potter, J. Org. Chem. 1995, 60, 4970; b) C. Liu, B. V. L. Potter, J. Org. Chem. 1997, 62, 8335; c) A. M. Riley, B. V. L. Potter, Tetrahedron Lett. 1999, 40, 2213; d) H. Sun, G. B. Reddy, C. George, E. J. Meuillet, M. Berggren, G. Powis, A. P. Kozikowski, Tetrahedron Lett. 2002, 43, 2835; e) D. J. Jenkins, A. M. Riley, B. V. L. Potter, J. Org. Chem. 1996, 61, 7719; f) A. P. Kozikowski, A. H. Fauq, G. Powis, D. C. Melder, J. Am. Chem. Soc. 1990, 112, 4528; g) A. B. Cheikh, L. E. Craine, J. Zemlicka, M. H. Heeg, Carbohydr. Res. 1990, 199, 19; h) A. Schnaars, C. Schultz, Tetrahderon 2001, 57, 519.
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18. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
19. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
20. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
21. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
22. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
23. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
24. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
25. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
26. For recent synthetic studies on inositols, see: a) Y. U. Kwon, C. Lee, S. K. Chung, J. Org. Chem. 2002, 67, 3327; b) H. Takahashi, H. Kittaka, S. Ikegami, J. Org. Chem. 2001, 66, 2705; c) K. S. Kim, J. I. Park, H. K. Moon, H. Yi, Chem. Commun. 1998,1945; d) Y. Landias, Chimia 1998, 52, 104; e) A. M. Riley, D. J. Jenkins, B. V. L. Potter, Carbohydr. Res. 1998, 314, 277; f) W. Motherwell, A. S. Williams, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2031; g) T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc. Perkin Trans. 1 1994, 1553; h) C. Jaramillo, M. M. Lomas, Tetrahedron Lett. 1991, 32, 2501.
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