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1
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0021750054
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For reviews dealing with chemistry and the biology of inositols, see:
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For reviews dealing with chemistry and the biology of inositols, see:. Berridge M.J., and Irvine R.F. Nature 312 (1984) 315-321
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Berridge, M.J.1
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Taylor C.W. Cell 111 (2002) 767-769
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Friedman S.D., Dager S.R., Parow A., Hirashima F., Demopulos C., Stoll A.L., Lyoo I.K., Dunner D.L., and Renshaw P.F. Biol. Psychiat. 56 (2004) 340-348
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Stoll, A.L.6
Lyoo, I.K.7
Dunner, D.L.8
Renshaw, P.F.9
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Coupland N.J., Ogilvie C.J., Hegadoren K.M., Seres P., Hanstock C.C., and Allen P.S. Biol. Psychiat. 57 (2005) 1526-1534
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Coupland, N.J.1
Ogilvie, C.J.2
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Seres, P.4
Hanstock, C.C.5
Allen, P.S.6
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Nestler J.E., Jakubowicz D.J., Reamer P., Gunn R.D., and Allan G. N. Eng. J. Med. 340 (1999) 1314-1320
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Islam, L.6
Nestler, J.E.7
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30
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0025003488
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For selected references on inositol analogues, see:
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For selected references on inositol analogues, see:. Kozikowski A.P., Fauq A.H., Powis G., and Melder D.C. J. Am. Chem. Soc. 112 (1990) 4528-4531
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(1990)
J. Am. Chem. Soc.
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Kozikowski, A.P.1
Fauq, A.H.2
Powis, G.3
Melder, D.C.4
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Sun H., Reddy G.B., George C., Meuillet E.J., Berggren M., Powis G., and Kozikowski A.P. Tetrahedron Lett. 43 (2002) 2835-2838
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Sun, H.1
Reddy, G.B.2
George, C.3
Meuillet, E.J.4
Berggren, M.5
Powis, G.6
Kozikowski, A.P.7
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40
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Kireev A.S., Nadein O.N., Agustin V.J., Bush N.E., Evidente A., Manpadi M., Ogasawara M.A., Rastogi S.K., Rogelj S., Shors S.T., and Kornienko A. J. Org. Chem. 71 (2006) 5694-5707
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Kireev, A.S.1
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Evidente, A.5
Manpadi, M.6
Ogasawara, M.A.7
Rastogi, S.K.8
Rogelj, S.9
Shors, S.T.10
Kornienko, A.11
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45
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0034700565
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We have been concurrently interested in the synthesis of polycyclic polyoxygenated molecular scaffolds which are based on fused cyclohexane rings and are known for their wide-ranging biological activity, see:
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We have been concurrently interested in the synthesis of polycyclic polyoxygenated molecular scaffolds which are based on fused cyclohexane rings and are known for their wide-ranging biological activity, see:. Mehta G., and Ramesh S.S. Chem. Commun. (2000) 2429-2430
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Ramesh, S.S.2
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Paul, B.J.1
Willis, J.2
Martinot, T.A.3
Ghiviriga, I.4
Abboud, K.A.5
Hudlicky, T.6
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Mehta, G.1
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Chopra, D.4
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62
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Fitton, P.2
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Angew. Chem., Int. Ed. Engl.
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Vogel, E.1
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Gunther, H.4
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67
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0037019971
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While the stereoselectivity noted during the bromination of 15 may be regarded as an extension of the well-known Fürst-Plattner rule for epoxide ring opening (see Ref. 14), an explanation for the regioselectivity observed in the same reaction is far less obvious. Putatively, the regioselectivity observed here may be attributed to a greater through-space electronic stabilization of the incipient bromonium ion by one or other of the two homoallylic hydroxy groups present in 15. See:
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While the stereoselectivity noted during the bromination of 15 may be regarded as an extension of the well-known Fürst-Plattner rule for epoxide ring opening (see Ref. 14), an explanation for the regioselectivity observed in the same reaction is far less obvious. Putatively, the regioselectivity observed here may be attributed to a greater through-space electronic stabilization of the incipient bromonium ion by one or other of the two homoallylic hydroxy groups present in 15. See:. Chiappe C., De Rubertis A., Jaber A., Lenoir D., Wattenbach C., and Pomelli C.S. J. Org. Chem. 67 (2002) 7066-7074
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J. Org. Chem.
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Chiappe, C.1
De Rubertis, A.2
Jaber, A.3
Lenoir, D.4
Wattenbach, C.5
Pomelli, C.S.6
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70
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71749083738
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Fürst, A.; Plattner, P. A. Abstr. Papers Int. Congr. Pure Appl. Chem., 12th, New York, 1951, 40.
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Fürst, A.; Plattner, P. A. Abstr. Papers Int. Congr. Pure Appl. Chem., 12th, New York, 1951, 40.
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72
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71749085387
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note
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+: 419.0317; found: 419.0353; 32 mp 220 °C (chars before melting); IR
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73
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71749110866
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note
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2 = 0.0758 for 3045 observed reflections, CCDC 752351.
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74
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71749090540
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note
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The mechanism for the acid-catalyzed rearrangement ('acetate dance') is shown below:{A figure is presented}.
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