1,4-di-O-methyl-myo-inositol, a natural product, was synthesised starting from p-benzoquinone. The treatment of 5,6-dibromocyclohex-2-ene-1,4-diol with Na/ROH-system afforded a C2-symmetric conduritol-B derivative key intermediate followed by acetylation. The OsO4 oxidation and followed by acetylation gave the tetraacetates. The hydrolysis of the acetate groups furnished the desired the myo-inositol derivatives in high yield.
(a) PosternakS., C. R. Acad. Sci., 1919, 169, 138; (b) T. Posternak, Chemistry of the cyclitols–the cyclitols, 1965. Hermann, Paris.
2.
(a) BillingtonD.C., Chem. Soc. Rev., 1989, 18, 83; (b) H. Streb, R.F. Irvine, M.J. Berridge and I. Schulz, Nature, 1983, 306, 67.
3.
(a) BerridgeM.J., Nature, 1993, 361, 315; (b) M.J. Berridge, P. Lipp and M.D. Bootman, Nat. Rev. Mol. Cell Biol., 2000, 1, 11; (c) S.J. Mills and B.V.L. Porter, Bioorg. Med. Chem., 2003, 11, 4245.
4.
SureshanK.M., MurakamiT., and WatanabeY., Synlett, 2005, 5, 769.
5.
GallagherR.T., Phytochemistry, 1975, 14, 755.
6.
PlouvierV., Compt. Rend., 1955, 241, 765.
7.
(a) StadelmaierA., and SchmidtR.R., Carbohydr. Res., 2003, 338, 2557; (b) P. Dittrich and N. Schilling, Phytochemistry, 1988, 27, 773; (c) A. Aguilo, M.M. Lomas and S. Penades, Tetrahedron Lett., 1992, 33, 401; (d) S.J. Angyal and V. Bender, J. Chem. Soc., 1961, 4718; (e) L. Anderson, The carbohydrates, chemistry and biochemistry, 2nd edn.; PigmanW., and HortonD., Eds.; Academic Press, New York, 1972, vol. 1A, pp. 519; (f) G.G. Post and L. Anderson, J. Am. Chem. Chem. Soc., 1962, 84, 471; and 478.
(a) AltenbachH.J., StegelmeierH., and VogelE., Tetrahedron Lett., 1978, 3333; (b) A.E. Gal and J.P. Voorstad, J. Labelled Compd. Radiopharm., 1987, 24, 397; (c) L. Kelebekli, Ü. Demir, Y. Kara, J. Chem. Res. (S), 1997, 11, 402.
11.
(a) LindstromU.M., FranckowiakR., PinaultN., and SomfaiP., Tetrahedron Lett., 1997, 38, 2027; (b) A.M. Boaz, Tetrahedron Asymmetry, 1995, 6, 15; (c) A.M. Ross, T.M. Pohl, K. Piazza, M. Thomas, B. Fox and D.L. Whalen, J. Am. Chem. Soc., 1982, 104, 1658; (d) R.J.K. Taylor, A.H. Haines and Z-X. Guo, Synlett, 1993, 607; (e) T. Hudlicky, H. Luna, H.F. Olivo, C. Anderson, T. Nugent and J.D. Price, J. Chem. Soc. Perkin Trans. 1, 1991, 2907; (f) S.T. Murphy, J.R. Bencsik and C.R. Johnson, Org. Lett., 1999, 1, 1483.
12.
TsuangW.S., GriffinG.W., HorningM.G., and StillwellW.G., J. Org. Chem., 1982, 47, 5339; (b) T. Esser, F. Farkas, S. Mangholz and U. Sequin, Tetrahedron, 1994, 50, 3709; (c) T. Esser and U. Sequin, Tetrahedron Lett., 1988, 29, 4405.
13.
BlockO., KleinG., and AltenbachH.J., J. Org. Chem., 2000, 65, 716.
14.
AdeltS., PlettenburgR., StrickerR., ReiserG., AltenbachH. J., and VogelG., J. Med. Chem., 1999, 42, 1262.
15.
(a) PlettenburgO., AdeltS., VogelG., and AltenbachH.J., Tetrahedron Asymmetry, 2000, 11, 1057; (b) S. Adelt, O. Plettenburg, G. Dallmann, F.P. Ritter, S.B. Shears, H.J. Altenbach and G. Vogel, Bioorg. Med. Chem. Lett., 2001, 11, 2705; (c) M. Podeschwa, O. Plettenburg, vom J. Brocke, O. Block, S. Adelt, H.J. Altenbach and G. Vogel, Eur. J. Org. Chem., 2003, 1958; (d) M.A.L. Podeschwa, O. Plettenburg and H.J. Altenbach, Eur. J. Org. Chem., 2005, 3101.
16.
CerèV., MatovaniG., PeriF., PollicinoS., and RicciA., Tetrahedron, 2000, 56, 1225.
