Resolution of synthetically useful myo-inositol derivatives using the chiral auxiliary O-acetylmandelic acid

Tetrahedron Asymmetry

Volumn 16, Issue 1, 2005, Pages 231-241

  Sureshan, Kana M ^a   Kiyosawa, Yoko ^a   Han, Fushe ^a   Hyodo, Sayuri ^a   Uno, Yuhki ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 O CYCLOHEXYLIDENE INOSITOL; 1,2 O ISOPROPYLIDENE INOSITOL; CHLORINE DERIVATIVE; DEXTRO 1,2 DI O ISOPROPYLIDENE INOSITOL; DEXTRO 1,2 O CYCLOHEXYLIDENE INOSITOL; DEXTRO 1,2:4,5 DI O CYCLOHEXYLIDENE INOSITOL; DEXTRO 1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; DEXTRO 1,4,5,6 TETRA O BENZOYLINOSITOL; DEXTRO 3,6 DI O (O ACETYLMANDELOYL) 1,2 DI O ISOPROPYLIDENE INOSITOL; DEXTRO 3,6 DI O (O ACETYLMANDELOYL) 1,2:4,5 DI O CYCLOHEXYLIDENE INOSITOL; DEXTRO 3,6 DI O (O ACETYLMANDELOYL) 1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; DEXTRO LEVO (O ACETYLMANDELOYL) 1,2 O CYCLOHEXYLIDENE 3,4 O (TETRAISOPROPYLDISILOXAN 1,3 DIYL)INOSITOL; DIBENZYL [DEXTRO 6 O (O ACETYLMANDELOYL) 1,2 O CYCLOHEXYLIDENE 3,4 O (TETRAISOPROPYLDISILOXAN 1,3 DIYL)INOSITOL] 5 PHOSPHATE; DIBENZYL [LEVO 6 O (O ACETYLMANDELOYL) 1,2 O CYCLOHEXYLIDENE 3,4 O (TETRAISOPROPYLDISILOXAN 1,3 DIYL)INOSITOL] 5 PHOSPHATE; INOSITOL DERIVATIVE; LEVO 1,2 DI O ISOPROPYLIDENE INOSITOL; LEVO 1,2 O CYCLOHEXYLIDENE INOSITOL; LEVO 1,2:4,5 DI O CYCLOHEXYLIDENE INOSITOL; LEVO 1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; LEVO 1,4,5,6 TETRA O BENZOYLINOSITOL; LEVO 3,6 DI O (O ACETYLMANDELOYL) 1,2 DI O ISOPROPYLIDENE INOSITOL; LEVO 3,6 DI O (O ACETYLMANDELOYL) 1,2:4,5 DI O CYCLOHEXYLIDENE INOSITOL; LEVO 3,6 DI O (O ACETYLMANDELOYL) 1,2:4,5 DI O ISOPROPYLIDENE INOSITOL; MANDELIC ACID DERIVATIVE; O ACETYLMANDELIC ACID; PROTON; PYRIDINE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHIRALITY; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; INTERMETHOD COMPARISON; LOW TEMPERATURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION;

EID: 12344263624     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.030     Document Type: Article

References (58)

1. M.J. Berridge Nature 361 1993 315
2. K. Hinchliffe, and R. Irvine Nature 390 1997 123
3. Phosphoinositides: Chemistry, Biochemistry and Biomedical applications; Bruzik, K. S. Ed; ACS symposium Series 718, ACS, Washington, 1999
4. M.A.J. Ferguson, and A.F. Williams Annu. Rev. Biochem. 57 1988 285
5. L. Qiao, F. Nan, M. Kunkel, A. Gallegos, and A.P. Kozikowski J. Med. Chem. 41 1998 3303
6. A.P. Kozikowski, A.H. Fauq, G. Powis, I.A. Aksoy, D.C. Melder, S. Aksoy, and H. Eichinger Cancer Chemother. Pharmacol. 29 1991 95
7. A.P. Kozikowski, A.H. Fauq, G. Powis, I.A. Aksoy, and M.J. Seewald J. Am. Chem. Soc. 112 1990 7403
8. M.C. Hewitt, D.A. Snyder, and P.H. Seeberger J. Am. Chem. Soc. 124 2002 13434
9. Y.-K. Kwon, C. Lee, and S.-K. Chung J. Org. Chem. 67 2002 3327
10. T. Suzuki, S.T. Suzuki, I. Yamada, Y. Koashi, K. Yamada, and N. Chida J. Org. Chem. 67 2002 2874
11. N. Chida, and S. Ogawa Chem. Commun. 1997 807 and reference cited therein
12. T. Suzuki, S. Tanaka, I. Yamada, Y. Koashi, K. Yamada, and N. Chida Org. Lett. 2 2000 1137
13. N. Chida, M. Yoshinaga, T. Tobe, and S. Ogawa Chem. Commun. 1997 1043
14. T. Akiyama, M. Ohnari, H. Shima, and S. Ozaki Synlett 1991 831
15. K.M. Sureshan, M.S. Shashidhar, T. Praveen, and T. Das Chem. Rev. 103 2003 4477
16. K.M. Sureshan, T. Miyasou, S. Miyamori, and Y. Watanabe Tetrahedron: Asymmetry 15 2004 3357
17. B.M. Trost, J.L. Belletire, S. Godleski, P.G. McDougal, and J.M. Balkovec J. Org. Chem. 51 1986 2370
18. For the use of OAM for the resolution of inositol derivatives: A.M. Riley, and B.V.L. Potter Tetrahedron Lett. 40 1999 2213
19. G. Horne, and B.V.L. Potter Chem. Eur. J. 7 2001 80
20. N. Chida, E. Yamada, and S. Ogawa J. Carbohydr. Chem. 7 1988 555
21. S.J. Mills, C. Liu, and B.V.L. Potter Carbohydr. Res. 337 2002 1795
22. S.J. Mills, and B.V.L. Potter J. Chem. Soc., Perkin Trans. 1 1997 1279
23. P.J. Garegg, B. Lindberg, I. Kvarnstrom, and S.C.T. Svensson Carbohydr. Res. 139 1985 209
24. S.J. Mills, and B.V.L. Potter J. Org. Chem. 61 1996 8980
25. S.J. Mills, K. Backers, C. Erneux, and B.V.L. Potter Org. Biomol. Chem. 1 2003 3546
26. N. Chida, K. Koizumi, Y. Kitada, C. Yokoyama, and S. Ogawa J. Chem. Soc., Chem. Commun. 1994 111
27. S.-K. Chung, and Y. Ryu Carbohydr. Res. 258 1994 145
28. S.-K. Chung, Y.-T. Chang, and Y. Ryu Pure Appl. Chem. 68 1996 931
29. M.S. Shashidhar, J.J. Volwerk, O.H. Griffith, and J.F.W. Keana Chem. Phys. Lipids 60 1991 101
30. J.G. Ward, and R.C. Young Tetrahedron Lett. 29 1988 6013
31. J. Gigg, R. Gigg, S. Payne, and R. Conant J. Chem. Soc., Perkin Trans. 1 1987 423
32. C. Liu, and B.V.L. Potter J. Org. Chem. 62 1997 8335
33. A.P. Kozikowski, A.H. Fauq, R.A. Wilcox, and S.R. Nahorski J. Org. Chem. 59 1994 2279
34. K.S. Ravikumar, and D. Farquhar Tetrahedron Lett. 43 2002 1367
35. Y. Watanabe, Y. Kiyosawa, A. Tatsukawa, and M. Hayashi Tetrahedron Lett. 42 2001 4641
36. L. Ling, and S. Ozaki Tetrahedron Lett. 34 1993 2501
37. L. Ling, and S. Ozaki Carbohydr. Res. 256 1994 49
38. T. Akiyama, N. Takechi, S. Ozaki, and K. Shiota Bull. Chem. Soc. Jpn. 65 1992 366
39. K.S. Sadovnikova, Z.P. Kuznetsova, V.I. Shvets, and R.P. Evstigneeva Zh. Org. Khim. 11 1975 1201 (Engl), 1211 (Russian)
40. 8e case
41. K.M. Sureshan, T. Miyasou, M. Hayashi, and Y. Watanabe Tetrahedron: Asymmetry 15 2004 3
42. K.M. Sureshan, T. Miyasou, and Y. Watanabe Carbohydr. Res. 339 2004 807
43. K.S. Bruzik, J. Myers, and M.-D. Tsai Tetrahedron Lett. 33 1992 1009
44. S. David, and S. Hanessian Tetrahedron 41 1985 643
45. J. Gigg, R. Gigg, and E. Martin-Zamora Tetrahedron Lett. 34 1993 2827
46. Y. Watanabe, M. Mitani, T. Morita, and S. Ozaki J. Chem. Soc., Chem. Commun.. 1989 482
47. Y. Watanabe, and M. Nakatomi Tetrahedron 55 1999 9743
48. F. Han, M. Hayashi, and Y. Watanabe Chem. Lett. 32 2003 46
49. F. Han, M. Hayashi, and Y. Watanabe Chem. Lett. 32 2003 724
50. F. Han, M. Hayashi, and Y. Watanabe Tetrahedron 59 2003 7703
51. F. Han, M. Hayashi, and Y. Watanabe Eur. J. Org. Chem. 2004 558
52. K.M. Sureshan, M.S. Shashidhar, and A.J. Varma J. Org. Chem. 67 2002 6884 and reference cited therein
53. A. Hosoda, Y. Miyake, E. Nomura, and H. Taniguchi Chem. Lett. 32 2003 1042
54. T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto, and K. Yamaguchi Chem. Commun. 2003 1734
55. K.M. Sureshan, R.G. Gonnade, M.S. Shashidhar, V.G. Puranik, and M.M. Bhadbhade Chem. Commun. 2001 881
56. T. Akiyama, H. Nishimoto, K. Ishikawa, and S. Ozaki Chem. Lett. 1992 447
57. T. Akiyama, N. Horiguchi, T. Ida, and S. Ozaki Chem. Lett. 1995 975
58. M. Jones, K.K. Rana, J.G. Ward, and R.C. Young Tetrahedron Lett. 30 1989 5353