References
- Berridge , M. J. and Irvine , R. F. 1989 . Nature , 341 : 197
- Saltiel , A. R. and Cuatrecasas , P. 1988 . Am. J. Physiol. , 255 : C1
- Billington , D. C. 1989 . Chem. Soc. Rev. , 18 : 83
- Bruzik , K. S. , Myers , J. and Tsai , M.-D. 1992 . Tetrahedron Lett. , 33 : 1009
- Aguiló , A. , Martín-Lomas , M. and Penadés , S. 1992 . Tetrahedron Lett. , 33 : 401
- Plourde , R. , d'Alarcao , M. and Saltiel , A. R. 1992 . J. Org. Chem. , 57 : 2606
- 1989 . Eur. J. Biochem. , 180 : 485 By this system all myo-inositol derivatives are named and numbered as D-myo-inositols regardless of whether the substituents occupy the lowest numbered positions in the resulting name. For example, the enantiomer of D-myo-inositol 1-phosphate is D-myo-inositol 3-phosphate (not L-myo-inositol 1-phosphate)In this communication we are using the stereospecific numbering system for myo-inositol described by the International Union of Biochemistry:
- Vacca , J. P. , de Solms , S. J. , Huff , J. R. , Billington , D. C. , Baker , R. , Kulagowski , J. J. and Mawer , I. M. 1989 . Tetrahedron , 45 : 5679 Compound 1 and its enantiomer have been prepared enantioselectively previously:
- 1991 . Tetrahedron , 47 : 907 corrected optical rotation measurements were reported later
- Garegg , P. J. , Iversen , T. , Johansson , R. and Lindberg , B. 1984 . Carbohydr Res. , 130 : 322
- Jiang , C. and Baker , D. C. 1986 . J. Carbohydr Chem. , 5 : 615 We substituted comercially available (American Tokyo Kasei, Inc., Portland OR.) 1,1-dimethoxycyclohexane for 1-ethoxycyclohexene in the synthesis of 2. See also:
- Yu , K.-L. and Fraser-Reid , B. 1988 . Tetrahedron Lett. , 29 : 979
- David , S. and Hanessian , S. 1985 . Tetrahedron , 41 : 643
- The dimer shown, 5, incorporates two molecules of inositol diol 2 with the same absolute configuration. It is also possible that the dimer formed in the the presence of the racemic 2 incorporates two diols of opposite absolute configuration. This possibility does not affect the rationalization suggested to account for the observed regiochemistry of acylation and alkylation
- Vacca , J. P. , de Solms , S. J. and Huff , J. R. 1987 . J. Am. Chem. Soc. , 109 : 3478
- Clark , T. M. and Switzer , R. L. 1977 . Experimental Biochemistry, , 2ed. , 161 – 2 . San Francisco : Freeman W. H. .