Quest for inosito-inositols: Synthesis of novel, annulated and conformationally locked inositols

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3105-3108

  Mehta, Goverdhan ^a   Ramesh, Senaiar S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; INOSITOL DERIVATIVE; NAPHTHALENE;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037424732     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00516-1     Document Type: Article

References (29)

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4. Mehta G., Ramesh S.S. Tetrahedron Lett. 42:2001;1987.
5. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
6. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
7. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
8. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
9. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
10. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
11. For some important references dealing with the chemistry and biology of inositols, see: (a) Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315; (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197; (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1; (d) Berridge, M. J. Nature 1993, 361, 315; (e) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933; (f) Hinterding, K.; Díaz, D. A.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 688; (g) Chang, Y.-T.; Rosania, G. R.; Chung, S.-K. Exp. Opin. Ther. Patents 2001, 11, 1.
12. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
13. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
14. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
15. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
16. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
17. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
18. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
19. Selected references on efforts to prepare new inositol analogues: (a) Kozikowski, A. P.; Fauq, A.H.; Powis, G.; Melder, D. C. J. Am. Chem. Soc. 1990, 112, 4528; (b) Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1995, 60, 4970; (c) Liu, C.; Potter, B. V. L. J. Org. Chem. 1997, 62, 8335; (d) Riley, A. M.; Potter, B. V. L. Tetrahedron Lett. 1999, 40, 2213; (e) Sun, H.; Reddy, G. B.; George, C.; Meuillet, E. J.; Berggren, M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2002, 43, 2835; (f) Cheikh, A. B.; Craine, L. E.; Zemlicka, J.; Heeg, M. H. Carbohydr. Res. 1990, 199, 19; (g) Schnaars, A.; Schultz, C. Tetrahedron 2001, 57, 519; (h) Paul, B. J.; Willis, J.; Martinot, T. A.; Ghivriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416.
20. Mehta, G.; Ramesh, S. S.; Bera, M. K. Chem. Eur. J. in press.
21. The stereochemistry of the syn- and anti-epoxides in each case was secured on the basis of X-ray crystal structure determination of anti-diacetate 11 (Fig. 1.
22. ++1).
23. de Souza S.E., Kee A., O'Brien P., Watson S.T. Tetrahedron Lett. 40:1999;387.
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26. Stereostructures of compounds 14-17 were secured through the X-ray crystal structure determination of the acetonide (A) derived from the diol derived from 14 (Fig. 2.
27. Angyal S.J., Craig D.C. Carbohydr. Res. 263:1994;149.
28. Bicyclic cyclohexadiene 21 is an annulated cyclohexadiene trans-diol derivative related to those derived from the aromatics employing recombinant E. coli cells and can be a versatile substrate in the synthesis. See, Franke D., Sprenger G.A., Muller M. Angew. Chem., Int. Ed. Engl. 40:2001;555.
29. Jeffrey G.A., Yeon Y. Carbohydr. Res. 159:1987;211.