Total synthesis, from D-xylose, of chiral, ring-contracted 1D-myo-inositol 1,4,5-trisphosphate and 1,3,4,5-tetrakisphosphate analogues with C-2 excised

Abstract

A route to chiral, cyclopentane-based congeners of the second messenger 1D-myo-inositol 1,4,5-trisphosphate and its enigmatic metabolite 1D-myo-inositol 1,3,4,5-tetrakisphosphate, starting from D-xylose, is described. Reaction of allyl α-D-xylopyranoside 7 with 2,2,3,3-tetramethoxybutane gave a 1∶1 mixture of the 2,3- and 3,4-butanediacetal-protected derivatives 8 and 9. The latter was converted in four steps into 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-D-xylopyranose 15, which on reduction with sodium borohydride gave 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-D-xylitol 16. Swern oxidation followed by samarium(II) iodide-mediated pinacol coupling gave a 1∶3 mixture of 1L-1,2,3,4/5-1-benzyloxy-2,3-dihydroxy-4,5-bis-(p-methoxybenzyloxy)cyclopentane 18 and 1L-1,2,4/3,5-3-benzyloxy-1,2-dihydroxy-4,5-bis-(p-methoxybenzyloxy)cyclopentane 19. The identity of the latter was confirmed by conversion into known compounds, and further elaboration gave the target compounds, 1D-1,2,4/3,5-cyclopentanepentaol 1,3,4-trisphosphate 5 and 1D-1,2,4/3,5-cyclopentanepentaol-1,2,3,4-tetrakisphosphate 6.

References

1. M. J. Berridge, Nature (London), 1993, 361, 315.
2. T. C. Südhof, C. L. Newton, B. T. Archer III, Y. A. Ushkaryov and G. A. Mignery, EMBO J., 1991, 10, 3199; O. Blondel, J. Takeda, H. Janssen, S. Seino and G. I. Bell, J. Biol. Chem., 1993, 268, 11 356; C. A. Ross, S. K. Danoff, M. J. Schell, S. H. Snyder and A. Ullrich, Proc. Natl. Acad. Sci. USA, 1992, 89, 4265; T. Monkawa, A. Miyawaki, T. Sugiyama, H. Yoneshima, M. Yamamoto-Hino, T. Furuichi, T. Saruta, M. Hasegawa and K. Mikoshiba, J. Biol. Chem., 1995, 270, 14 700.
3. I. R. Batty, S. R. Nahorski and R. F. Irvine, Biochem. J., 1985, 232, 211.
4. P. J. Cullen, A. P. Dawson and R. F. Irvine, Biochem. J., 1995, 305, 139.
5. P. J. Cullen, J. J. Hsuan, O. Truong, A. J. Letcher, T. R. Jackson, A. P. Dawson and R. F. Irvine, Nature (London), 1995, 376, 527.
6. B. V. L. Potter and D. Lampe, Angew. Chem., Int. Ed. Engl., 1995, 34, 1933.
7. A. M. Riley, D. J. Jenkins and B. V. L. Potter, J. Am. Chem. Soc., 1995, 117, 3300.
8. D. J. Jenkins, A. M. Riley and B. V. L. Potter, J. Org. Chem., 1996, 61, 7719.
9. J. L. Chiara, W. Cabri and S. Hanessian, Tetrahedron Lett., 1991, 32, 1125.
10. E. Perrin, J.-M. Mallet and P. Sinaÿ, Carbohydr. Lett., 1995, 1, 215.
11. K. Fukase, S. Hase, T. Ikenaka and S. Kusumoto, Bull. Chem. Soc. Jpn., 1992, 65, 436.
12. N. Moitessier, F. Chrétien, Y. Chapleur and C. Humeau, Tetrahedron Lett., 1995, 36, 8023.
13. M. E. Haque, T. Kikuchi, K. Yoshimoto and Y. Tsuda, Chem. Pharm. Bull., 1985, 33, 2243.
14. J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem., 1996, 61, 3897.
15. (a) J. J. Naleway, C. R. H. Raetz and L. Anderson, Carbohydr. Res., 1988, 179, 199; (b) S. Rio, J.-M. Beau and J.-C. Jacquinet, Carbohydr. Res., 1991, 219, 71.
16. K. Takeo, M. Nakagen, Y. Teramoto and Y. Nitta, Carbohydr. Res., 1990, 201, 261; R. F. Helm, J. Ralph and L. Anderson, J. Org. Chem., 1991, 56, 7015; L. Ziser and S. G. Withers, Carbohydr. Res., 1994, 265, 9.
17. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke and S. L. Warriner, J. Chem. Soc., Perkin Trans. 1, 1997, 351.
18. D. J. Jenkins and B. V. L. Potter, Carbohydr. Res., 1996, 287, 169.
19. M. Carpintero, A. Fernández-Mayoralas and C. Jaramillo, J. Org. Chem., 1997, 62, 1916.
20. J. Gigg and R. Gigg, J. Chem. Soc. C, 1966, 82; T. Desai, J. Gigg, R. Gigg and E. Martín-Zamora, Carbohydr. Res., 1994, 262, 59.
21. S. Takahashi, T. Kinoshita and M. Takahashi, J. Antibiot., 1994, 47, 95; M. Takahashi, K. Tanzawa and S. Takahashi, J. Biol. Chem., 1994, 269, 369.
22. K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651.
23. H. Z. Sable, T. Anderson, B. Tolbert and T. Posternak, Helv. Chim. Acta, 1963, 46, 1157.
24. S. J. Angyal and B. M. Luttrell, Aust. J. Chem., 1970, 23, 1831.
25. J. L. Chiara and M. Martín-Lomas, Tetrahedron Lett., 1994, 35, 2969.
26. K.-L. Yu and B. Fraser-Reid, Tetrahedron Lett., 1988, 29, 979.
27. A. P. Briggs, J. Biol. Chem., 1922, 53, 13.
28. D. A. Sawyer and B. V. L. Potter, J. Chem. Soc., Perkin Trans. 1, 1992, 923.
29. T. Ogawa, Y. Takahashi and M. Matsui, Carbohydr. Res., 1982, 102, 207.
30. S. Ozaki, Y. Kondo, N. Shiotani, T. Ogasawara and Y. Watanabe, J. Chem. Soc., Perkin Trans. 1, 1992, 729; T. Desai, J. Gigg, R. Gigg and E. Martín-Zamora, in Synthesis in Lipid Chemistry, ed. J. H. P. Tyman, Royal Society of Chemistry, London, 1996, pp. 67–92.
31. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.