Synthesis of natural PI(3,4,5)P3

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1583-1586

  Watanabe, Yutaka ^a   Nakatomi, Mitsunobu ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATIDYLINOSITOL; POLYPHOSPHOINOSITIDE;

ARTICLE; SYNTHESIS;

EID: 0032546217     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00034-3     Document Type: Article

References (22)

1. 1. Duckworth, B. C.; Cantley, L. C. PI 3-kinase and receptor-linked signal transduction; Bell, R. M.; Exton, J. H.; Prescott, S. M. Ed.; Handbook of Lipid Research, Plenum Press: New York, NY, 1996; Vol. 8, pp 125-175.
2. 1. Duckworth, B. C.; Cantley, L. C. PI 3-kinase and receptor-linked signal transduction; Bell, R. M.; Exton, J. H.; Prescott, S. M. Ed.; Handbook of Lipid Research, Plenum Press: New York, NY, 1996; Vol. 8, pp 125-175.
3. 2. a) Watanabe, Y.; Hajimu, H.; Ozaki, S. Tetrahedron Lett. 1994, 35, 123-124.
4. b) Gou, D.-M.; Chen, C.-S. J. Chem. Soc., Chem. Commun. 1994, 2125-2126.
5. c) Toker, A.; Meyer, M.; Reddy, K. K.; Falck, J. R.; Aneja, R.; Aneja, S.; Parra, A.; Burns, D. J.; Ballas, L. M.; Cantley, L. C. J. Biol. Chem. 1994, 269, 32358-32367.
6. d) Bruzik, K. S.; Kubiak, R. J. Tetrahedron Lett. 1995, 36, 2415-2418.
7. e) Watanabe, Y.; Tomioka, M.; Ozaki, S. Tetrahedron 1995, 51, 8969-8976.
8. f) Desai, T.; Gigg, J.; Gigg, R.; Martín-Zamora, E. Spec. Publ.-Royal Soc. of Chem. 1996, 180, 67-92.
9. g) Wang, D. S.; Chen, C. S. J. Org. Chem. 1996, 61, 5905-5910.
10. h) Aneja, S. G.; Parra, A.; Stoenescu, C.; Xia, W.; Aneja, R. Tetrahedron Lett. 1997, 38, 803-806.
11. i) Grove, S. J. A.; Holmes, A. B.; Painter, G. F.; Hawkins, P. T.; Stephens, L. R. J. Chem. Soc., Chem. Commun. 1997, 1635-1636.
12. 3. Watanabe, Y.; Nakamura, T.; Mitsumoto, H. Tetrahedron Lett. 1997, 38, 7407-7410.
13. 4. Alessi, D. R.; James, S. R.; Downes, C. P.; Holmes, A. B.; Gaffney, P. R. J.; Reese, C. B.; Cohen, P. Current Biology, 1997, 7, 261-269. Stokoe, D.; Stephens, L. R.; Copeland, T.; Gaffney, P. R. J.; Reese, C. B.; Painter, G. P.; Holmes, A. B.; McCormick, F.; Hawkins, P. T. Science, 1997, 277, 567-570. Synthetic detail has not appeared yet.
14. 4. Alessi, D. R.; James, S. R.; Downes, C. P.; Holmes, A. B.; Gaffney, P. R. J.; Reese, C. B.; Cohen, P. Current Biology, 1997, 7, 261-269. Stokoe, D.; Stephens, L. R.; Copeland, T.; Gaffney, P. R. J.; Reese, C. B.; Painter, G. P.; Holmes, A. B.; McCormick, F.; Hawkins, P. T. Science, 1997, 277, 567-570. Synthetic detail has not appeared yet.
15. 5. Watanabe, Y.; Mitani, M.; Morita, T.; Ozaki, S. J. Chem. Soc., Chem. Commun. 1989, 482-483.
16. 6. Chida, N.; Yamada, E.; Ogawa, S. J. Carbohydr. Chem. 1988, 7, 555-570.
17. 3)} of the substance 4 derived by the deacylation of the 6-l-menthoxyacetyl derivative 15. The specimen 4 was converted to the known 1D-1,2-O-cyclohexylidene-myo-inositol 16 [Sadovnikova, M. S.; Kuznetsova, Z. P.; Shvets, V. I.; Evstigneeva, R. P. Zh. Org. Khim. 1975, 11, 1211-1217, (1201-1206 for English version)] by treatment with tetrabutylammonium fluoride in THF and its absolute configuration was confirmed. (equation presented)
18. 8. Watanabe, Y.; Inada, E.; Jinno, M.; Ozaki, S. Tetrahedron Lett. 1993, 34, 497-500.
19. 9. Watanabe, Y. Selective Reactions and Total Synthesis of Inositol Phosphates; Rahman, A. Ed.; Elsevier: Amsterdam, 1996; Vol. 18, pp 391-456.
20. 3, 109 MHz) δ=-1.69 (1/2P), -1.59 (1/2P), -1.32 (1P), -0.86 (2P).
21. 11. van Boeckel C. A. A.; Beetz, T. Tetrahedron Lett., 1983, 24, 3775-3778.
22. 3N, 6:1:0.5) δ=-0.52, 0.81, 1.88, 2.86. FAB-MS (negative, diethanolamine) m/z 1125[M-1].