Chelation-Assisted C-O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s)

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8315-8318

  Yeh, Sue Min ^a   Lee, Gene Hsiang ^a   Wang, Yu ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001013850     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970606e     Document Type: Article

References (29)

1. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
2. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
3. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
4. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
5. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
6. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
7. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
8. For reviews, see: (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643. (b) Billington, D. C. Chem. Soc. Rev. 1989, 18, 83. (c) Potter, B. V. L. Nat. Prod. Rep. 1990, 1. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 10441. (e) Billington, D. C. The Inositol Phosphate Chemical-Synthesis and Biological Significance; VCH: New York, 1993. (f) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933. (g) Kiddle, J. J. Chem. Rev. (Washington, D.C.) 1995, 95, 2189. (h) Hudlicky, T.; Cebulak, M. Cyclitols And Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
9. (a) Greene, T. A.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991.
10. (b) Kocienski, P. J. Protective Groups; Thieme: New York, 1994.
11. (a) Vogl, O.; Anderson, B. C.; Simons, D. M. J. Org. Chem. 1969, 34, 204.
12. (b) Lee, H. W.; Kishi, Y.; J. Org. Chem. 1985, 50, 4402.
13. (c) Billington, D. C.; Baker, R. J. Chem. Soc., Chem. Commun. 1987, 1011.
14. (d) Baudin, G.; Glänzer, B. I.; Swaminathan, K. S.; Vasella, A. Helv. Chim. Acta 1988, 71, 1367.
15. (e) Gilbert, I. H.; Holmes, A. B.; Young, R. C. Tetrahedron Lett. 1990, 31, 2633.
16. (f) Gilbert, I. H.; Holmes, A. B.; Pestchanker, N. J.; Young, R. C. Carbohyd. Res. 1992, 234, 117.
17. (g) Andersch, P.; Schneider, M. P. Tetrahedron: Asymmetry 1993, 4, 2135.
18. (h) Li, C.; Vasella, A. Helv. Chim. Acta 1993, 76, 211.
19. (i) Banerjee, T.; Srikantiah, S. M. Tetrahedron Lett. 1994, 35, 8053.
20. (j) Ozaki, S.; Koya, Y.; Ling, L.; Watanabe, Y.; Kimura, Y.; Hirata, M. Bull. Chem. Soc., Jpn. 1994, 67, 1058.
21. For reviews, see: (a) Trofimov, B. A.; Korostova, S. E. Russ. Chem. Rev. 1975, 44, 41. (b) Mukaiyama T.; Murakami, M. Synthesis 1987, 1043. (c) Alexakis A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 7, 477. (d) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 635. (e) Luh, T.-Y. Synlett 1996, 201.
22. For reviews, see: (a) Trofimov, B. A.; Korostova, S. E. Russ. Chem. Rev. 1975, 44, 41. (b) Mukaiyama T.; Murakami, M. Synthesis 1987, 1043. (c) Alexakis A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 7, 477. (d) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 635. (e) Luh, T.-Y. Synlett 1996, 201.
23. For reviews, see: (a) Trofimov, B. A.; Korostova, S. E. Russ. Chem. Rev. 1975, 44, 41. (b) Mukaiyama T.; Murakami, M. Synthesis 1987, 1043. (c) Alexakis A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 7, 477. (d) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 635. (e) Luh, T.-Y. Synlett 1996, 201.
24. For reviews, see: (a) Trofimov, B. A.; Korostova, S. E. Russ. Chem. Rev. 1975, 44, 41. (b) Mukaiyama T.; Murakami, M. Synthesis 1987, 1043. (c) Alexakis A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 7, 477. (d) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 635. (e) Luh, T.-Y. Synlett 1996, 201.
25. For reviews, see: (a) Trofimov, B. A.; Korostova, S. E. Russ. Chem. Rev. 1975, 44, 41. (b) Mukaiyama T.; Murakami, M. Synthesis 1987, 1043. (c) Alexakis A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 7, 477. (d) Luh, T.-Y. Pure Appl. Chem. 1996, 68, 635. (e) Luh, T.-Y. Synlett 1996, 201.
26. These products were obtained as racemic mixture.
27. Yuan, T.-M.; Yeh, S.-M.; Hsieh, Y.-T.; Luh, T.-Y. J. Org. Chem. 1994, 59, 8192.
28. Yuan, T.-M.; Hsieh, Y.-T.; Yeh, S.-M.; Shyue, J.-J.; Luh, T.-Y. Synlett 1996, 53.
29. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.