A type 2 Ferrier rearrangement-based synthesis of d-myo-inositol 1,4,5-trisphosphate

Tetrahedron Asymmetry

Volumn 20, Issue 6-8, 2009, Pages 857-866

  Keddie, Neil S ^a   Bultynck, Geert ^b   Luyten, Tomas ^b   Slawin, Alexandra M Z ^a   Conway, Stuart J ^c  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 O BENZYL 2 HYDROXY 5 O(4 METHOXYBENZYL) 4 O TRIISOPROPYLSILYL 6 OXOCYCLOHEXYL ACETATE; CALCIUM ION; DEXTRO 1 O ACETYL 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL 5 O(4 METHOXYBENZYL) 4 O TRIISOPROPYLSILYL MYO INOSITOL; DEXTRO 1 O ACETYL 3 O BENZYL 5 O(4 METHOXYBENZYL) 4 O TRIISOPROPYLSILYL MYO INOSITOL; DEXTRO 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL 4 O TRIISOPROPYLSILYL MYO INOSITOL; DEXTRO 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL 5 O(4 METHOXYBENZYL) 4 O TRIISOPROPYLSILYL MYO INOSITOL; DEXTRO 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL 5 O(4 METHOXYBENZYL)MYO INOSITOL; DEXTRO 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL MYO INOSITOL; DEXTRO 3 O BENZYL 2,6 O BISBENZYLOXYMETHYL MYO INOSITOL 1,4,5 TRIS(DIBENZYL PHOSPHATE); DEXTRO MYO INOSITOL 1,4,5 TRIPHOSPHATE; DEXTRO MYO INOSITOL 1,4,5 TRIPHOSPHATE HEXAKIS SODIUM SALT; GLUCOSE DERIVATIVE; METHYL 2 O BENZYL 3 O TRIISOPROPYLSILYL 4,6 O ANISYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 O BENZYL 4 O(4 METHOXYBENZYL) 3 O TRIISOPROPYLSILYL ALPHA DEXTRO GLUCO HEXADIALDO 1,5 PYRANOSIDE; METHYL 2 O BENZYL 4 O(4 METHOXYBENZYL) 3 O TRIISOPROPYLSILYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 O BENZYL 4,6 O ANISYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE 3; METHYL 3 O BENZYL 4,6 O ANISYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 4,6 O ANISYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 O ACETYL 2 O BENZYL 4 O(4 METHOXYBENZYL) 3 O TRIISOPROPYLSILYL ALPHA DEXTRO GLUCOHEX 5 ENOPYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CHEMICAL STRUCTURE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 65549140099     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.03.006     Document Type: Article

References (53)

1. Berridge M.J., Bootman M.D., and Roderick H.L. Nat. Rev. Mol. Cell Biol. 4 (2003) 517-529
2. Conway S.J., and Miller G.J. Nat. Prod. Rep. 24 (2007) 687-707
3. Potter B.V.L., and Lampe D. Angew. Chem., Int. Ed. Engl. 34 (1995) 1933-1972
4. Morris S.A., Nerou E.P., Riley A.M., Potter B.V.L., and Taylor C.W. Biochem. J. 367 (2002) 113-120
5. Correa V., Riley A.M., Shuto S., Horne G., Nerou E.P., Marwood R.D., Potter B.V.L., and Taylor C.W. Mol. Pharmacol. 59 (2001) 1206-1215
6. Marwood R.D., Correa V., Taylor C.W., and Potter B.V.L. Tetrahedron: Asymmetry 11 (2000) 397-403
7. Marwood R.D., Shuto S., Jenkins D.J., and Potter B.V.L. Chem. Commun. (2000) 219-220
8. vanStraten N.C.R., vanderMarel G.A., and vanBoom J.H. Tetrahedron 53 (1997) 6509-6522
9. vanStraten N.C.R., vanderMarel G.A., and vanBoom J.H. Tetrahedron Lett. 37 (1996) 3599-3602
10. Takahashi M., Tanzawa K., and Takahashi S. J. Biol. Chem. 269 (1994) 369-372
11. Takahashi M., Kagasaki T., Hosoya T., and Takahashi S. J. Antibiot. 46 (1993) 1643-1647
12. Li W.H., Llopis J., Whitney M., Zlokarnik G., and Tsien R.Y. Nature 392 (1998) 936-941
13. Walker J.W., Feeney J., and Trentham D.R. Biochemistry 28 (1989) 3272-3280
14. Conway S.J., Thuring J.W., Andreu S., Kvinlaug B.T., Roderick H.L., Bootman M.D., and Holmes A.B. Aust. J. Chem. 59 (2006) 887-893
15. Li W.H., Schultz C., Llopis J., and Tsien R.Y. Tetrahedron 53 (1997) 12017-12040
16. Bello D., Aslam T., Bultynck G., Slawin A.M.Z., Roderick H.L., Bootman M.D., and Conway S.J. J. Org. Chem. 72 (2007) 5647-5659
17. Wang Y.L.K., Chen W., Blair D., Pu M.M., Xu Y.J., Miller S.J., Redfield A.G., Chiles T.C., and Roberts M.F. J. Am. Chem. Soc. 130 (2008) 7746-7755
18. Kayser-Bricker K.J., Jordan P.A., and Miller S.J. Tetrahedron 64 (2008) 7015-7020
19. Xu Y.J., Sculimbrene B.R., and Miller S.J. J. Org. Chem. 71 (2006) 4919-4928
20. Morgan A.J., Komiya S., Xu Y.J., and Miller S.J. J. Org. Chem. 71 (2006) 6923-6931
21. Sculimbrene B.R., Xu Y.J., and Miller S.J. J. Am. Chem. Soc. 126 (2004) 13182-13183
22. Morgan A.J., Wang Y.K., Roberts M.F., and Miller S.J. J. Am. Chem. Soc. 126 (2004) 15370-15371
23. Sculimbrene B.R., Morgan A.J., and Miller S.J. Chem. Commun. (2003) 1781-1785
24. Sculimbrene B.R., Morgan A.J., and Miller S.J. J. Am. Chem. Soc. 124 (2002) 11653-11656
25. Sculimbrene B.R., and Miller S.J. J. Am. Chem. Soc. 123 (2001) 10125-10126
26. Ferrier R.J. J. Chem. Soc., Perkin Trans. 1 (1979) 1455-1458
27. Ferrier R.J., and Middleton S. Chem. Rev. 93 (1993) 2779-2831
28. Takahashi H., Kittaka H., and Ikegami S. J. Org. Chem. 66 (2001) 2705-2716
29. Takahashi H., Kittaka H., and Ikegami S. Tetrahedron Lett. 39 (1998) 9707-9710
30. Peng J.R., and Prestwich G.D. Tetrahedron Lett. 39 (1998) 3965-3968
31. Chen J., and Prestwich G.D. J. Org. Chem. 63 (1998) 430-431
32. Chen J., Feng L., and Prestwich G.D. J. Org. Chem. 63 (1998) 6511-6522
33. Estevez V.A., and Prestwich G.D. J. Am. Chem. Soc. 113 (1991) 9885-9887
34. Bender S.L., and Budhu R.J. J. Am. Chem. Soc. 113 (1991) 9883-9885
35. Cleophax J., Dubreuil D., Gero S.D., Loupy A., Dealmeida M.V., Dasilva A.D., Vass G., Bischoff E., Perzborn E., Hecker G., and Lockhoff O. Bioorg. Med. Chem. Lett. 5 (1995) 831-834
36. Thum O., Chen J., and Prestwich G.D. Tetrahedron Lett. 37 (1996) 9017-9020
37. Gu Q.M., and Prestwich G.D. J. Org. Chem. 61 (1996) 8642-8647
38. Chen J., Profit A.A., and Prestwich G.D. J. Org. Chem. 61 (1996) 6305-6312
39. Jenkins D.J., Riley A.M., and Potter B.V.L. J. Org. Chem. 61 (1996) 7719-7726
40. Dubreuil D., Cleophax J., deAlmeida M.V., VerreSebrie C., Liaigre J., Vass G., and Gero S.D. Tetrahedron 53 (1997) 16747-16766
41. Jia Z.J., Olsson L., and Fraser-Reid B. J. Chem. Soc., Perkin Trans. 1 (1998) 631-632
42. Chung S.K., Yu S.H., and Chang Y.T. J. Carbohydr. Chem. 17 (1998) 385-390
43. Jenkins D.J., Dubreuil D., and Potter B.V.L. J. Chem. Soc., Perkin Trans. 1 (1996) 1365-1372
44. Evans D.A., Chapman K.T., and Carreira E.M. J. Am. Chem. Soc. 110 (1988) 3560-3578
45. Poon K.W.C., and Dudley G.B. J. Org. Chem. 71 (2006) 3923-3927
46. Erdahl W.L., Chapman C.J., Taylor R.W., and Pfeiffer D.R. Biophys. J. 66 (1994) 1678-1693
47. Chaney M.O., Demarco P.V., Jones N.D., and Occolowi J.l. J. Am. Chem. Soc. 96 (1974) 1932-1933
48. Koyama Y., Lear M.J., Yoshimura F., Ohashi I., Mashimo T., and Hirama M. Org. Lett. 7 (2005) 267-270
49. Moitessier N., Englebienne P., and Chapleur Y. Tetrahedron 61 (2005) 6839-6853
50. Johansson R., and Samuelsson B. J. Chem. Soc., Perkin Trans. 1 (1984) 2371-2374
51. Leung L.W., and Bittman R. Carbohydr. Res. 305 (1997) 171-179
52. Kasri N.N., Bultynck G., Smyth J., Szlufcik K., Parys J.B., Callewaert G., Missiaen L., Fissore R.A., Mikoshiba K., and de Smedt H. Mol. Pharmacol. 66 (2004) 276-284
53. Tovey S.C., Sun Y., and Taylor C.W. Nat. Prot. 1 (2006) 259-263