Chiro-inositols in organic synthesis

Mini-Reviews in Organic Chemistry

Volumn 6, Issue 1, 2009, Pages 1-8

  Singleton, J ^a   Hoberg, J O ^a  

^a UNIVERSITY OF WYOMING   (United States)

Author keywords

Asymmetric synthesis; D chiro inositol; L chiro inositol; Pinitol; Quebrachitol

Indexed keywords

ALCOHOLS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYOLS; SUGARS;

A-RINGS; ANOMERIC CARBON; ASYMMETRIC SYNTHESIS; D CHIRO INOSITOLS; ENANTIOMERIC PAIRS; L-CHIRO-INOSITOL; NATURALLY OCCURRING; ORGANIC SYNTHESIS; PINITOL; QUEBRACHITOL;

OXYGEN;

EID: 70049112495     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019309787316175     Document Type: Article

References (49)

1. Miethchen, R. J.; Sowa, C.; Frank, M.; Michalik, M.; Reinke, H. Carbohydr. Res., 2002, 337, 1-9.
2. Angyal, S. J.; Anderson, L.; Cahn, R. S.; Dawson, R. M. C.; Hoffmann-Ostenhof, O.; Klyne, W.; Posternak, T. Pure Appl. Chem., 1974, 37, 285-297.
3. IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature. Nomenclature of Cyclitols. Recommendations, 1973. Pure Appl. Chem., 1974, 37, 285-297.
4. Kiddle, J. J. Chem. Rev., 1995, 95, 2189-2202.
5. These materials can be obtained from various commercial suppliers at high cost, however pinitol can be purchased from New Zealand Pharmaceuticals and quebrachitol from the Rubber institute of Malaysia at reasonable prices.
6. Anderson, A. B. TAPPI, 1952, 35, 198.
7. Tegge, W.; Ballou, C. E. Proc. Natl. Acad. Sci. USA, 1989, 86, 94-98.
8. In brief, pinitol (10g) is heated to 100 °C in 15 mL of 47% HI using a Dean-Stark trap for 2-3h. Recrystallization from EtOH/MeOH (95:5) provides crystalline inositol.
9. Angyal, S. J.; James, K. Carbohydr. Res., 1970, 12, 147-149.
10. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev., 1996, 96, 1195.
11. Luchetti, G.; Ding, K.; D'Alarcao, M.; Kornienko, A. Synthesis, 2008, 3142-3147.
12. Komienko, A.; D'Alarcao, M. Tetrahedron Asymmetry, 1999, 10, 827-829.
13. Shintaro, S.; Rumiko, S.; Ryuichi, S. Chem. Pharm. Bull., 2004, 52, 727-732.
14. Jaramillo, C.; Chiara, J.-L.; Martin-Lomas, M. J. Org. Chem., 1994, 59, 3135-3141.
15. Takahashi, H.; Kittaka, H.; Ikegami, S. J. Org. Chem., 2001, 66, 2705-2716.
16. Berlin, W. K.; Zhang, W.-S.; Shen, T. Y. Tetrahedron, 1991, 47, 1.
17. Chung, S.-K.; Kwon, Y.-U. Bioorg. Med. Chem. Lett., 1999, 9, 2135-2138.
18. Takahashi, Y.; Nakayama, H.; Katagiri, K.; Ichikawa, K.; Ito, N.; Takita, T.; Takeuchi, T.; Miyake, T. Tetrahedron Lett., 2001, 42, 1053-1056.
19. Sureshan, K. M.; Watanabe, Y. Synlett, 2004, 493-496.
20. Catelani, G.; Corsaro, A.; D'Andrea, F.; Mariani, M.; Pistara, V. Bioorg. Med. Chem. Lett., 2002, 12, 3313-3315.
21. Miethchen, R. J. J. Carbohydr. Chem., 2003, 22, 801-825.
22. Cid, M. B.; Alfonso, F.; Martin-Lomas, M. Synlett, 2005, 2052-2056.
23. Cid, M. B.; Bonilla, J. B.; Dumarcay, S.; Alfonso, F.; Martín-Lomas, M. Eur. J. Org. Chem., 2002, 881-888.
24. Cousins, G.; Falshaw, A.; Hoberg, J. O. Carbohydr. Res., 2003, 338, 995-998.
25. Akiyama, T.; Nishimoto, H.; Kuwata, T.; Ozaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 180-188.
26. Angyal, S.; Irving, G.; Rutherford, D.; Tate, M. Aust. J. Chem., 1965, 6662-6664.
27. Liu, C.; Riley, A. M.; Yang, X.; Shears, S. B.; Potter, B. V. L. J. Med. Chem., 2001, 44, 2984-2989.
28. Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett., 1992, 447-450.
29. Akiyama, T.; Horiguchi, N.; Ida, T.; Ozaki, S. Chem. Lett., 1992, 975-976.
30. Akiyama, T.; Nishimoto, H.; Ozaki, S. Tetrahedron Lett., 1991, 32, 1335-1338.
31. Akiyama, T.; Okada, K.; Ozaki, S. Tetrahedron Lett., 1992, 33, 5763-5766.
32. Cousins, G.; Falshaw, A.; Hoberg, J. O. Org. Biomol., Chem., 2004, 2, 2272-2274.
33. Akiyama, T.; Hara, M.; Fuchibe, K.; Sakamoto, S.; Yamaguchi, K. Chem. Commun., 2003, 1734-1735.
34. Dong, Y.; Teesdale-Spittle, P.; Hoberg, J. O. Tetrahedron Lett., 2005, 46, 353-355.
35. Trost, B. M. J. Org. Chem., 2004, 69, 5813-5837.
36. Singleton, J. PhD thesis, University of Wyoming, Laramie, 2008.
37. Paul, B. J.; Hobbs, E.; Buccino, P.; Hudlicky, T. Tetrahedron Lett., 2001, 42, 6433-6435.
38. Falshaw, A.; Gainsford, G. J.; Lensink, C.; Slade, A. T.; Wright, L. J. Polyhedron, 2007, 26, 329-337.
39. Azev, V. N.; D'Alarcao, M. J. Org. Chem., 2004, 69, 4839-4842.
40. Painter, G. F.; Eldridge, P. J.; Falshaw, A. Bioorg. Med. Chem., 2004, 12, 225-232.
41. Painter, G. F.; Falshaw, A.; Wong, H. Org. Biomol. Chem., 2004, 2, 1007-1012.
42. Painter, G. F.; Falshaw, A. J. J. Chem. Soc. Perkin Trans. I, 2000, 1157.
43. Zhan, T.; Lou, H. Carbohydr. Res., 2007, 342, 865-869.
44. Cadenas, R. A.; Aguilar, G. J.; Gelpi, M. E. Carbohydr. Res., 1986, 148, 153-161.
45. Angyal, S.; Gilham, P. T. J. Chem. Soc., 1957, 3691-3699.
46. Falshaw, A.; Hart, J. B.; Tyler, P. C. Carbohydr. Res., 2000, 329, 301-308.
47. Bui, V. P.; Hudlicky, T. Tetrahedron, 2004, 60, 641-646.
48. Abraham, R. J.; Byrne, J. J.; Griffiths, L.; Koniotou, R. Magn. Reson. Chem., 2005, 43, 611-624.
49. Paulsen, H.; von Deyn, W.; Roben, W. Justus Liebigs Ann. Chem., 1984, 433-449.