338 INOSITOLS 



Mono- and dicarbonyl derivatives also have been prepared from the opti- 

 cally active isomers/- ^^- ^^ 



Conversions of one inositol isomer into another have frequently been 

 effected with the use of the keto derivatives as intermediaries. In this 

 manner, weso-inositol (V) has been converted to epf-inositol (11)^^ and 

 to scyllitol (VII) /^ and ?r?eso-inositol has been produced from d-inositol 

 (VIII). ^^ The preparation of aZ/o-inositol (III) and mwco-inositol (VI) from 

 the naturally occurring tetritol conduritoP° should also be mentioned. 

 Another type of conversion is carried out through the drastic action of 

 halogen acids at elevated temperature.^* Thus, meso-inositol (V) is con- 

 verted to dZ-inositol (VIII + IX). ®^' ^^ Corresponding reactions have also 

 been described with quebrachitol and Z-inositol (IX) as the starting pro- 

 ducts." 



The synthesis of meso-inositol by the catalytic hydrogenation of hexa- 

 hydroxybenzene^^ appears to have been repeated recently, ^^ although other 

 workers'"' '^ experienced difficulty in confirming it. 



Addendum: Among other literature reports, the following may be 

 mentioned : a new total synthesis of meso-inositol (V) f^ the demonstration 



OCH, 



of the structure of quebrachitol, a monomethyl ether of /-inositol (IX);'* 

 and a discussion of the nomenclature of the cyclitols and of some of their 

 isopropylidene derivatives.'* 



63 T. Posternak, Helv. Chim. Acta 24, 1045 (1941). 



" H. Muller, /. Chem. Soc. 91, 1780 (1907); 101, 2383 (1912). 



«*T. Posternak, Helv. Chim. Acta 31, 2242 (1948). 



66 H. G. Fletcher, Jr., and G. R. Findlay, /. Am. Chem. Soc. 70, 4050 (1948). 



6^ A. Contardi and B. Ciocca, Gazz. chim. ital. 79, 694 (1949). 



68 H. Wieland and R. S. Wishart, Ber. deul. chem. Ges. 47, 2082 (1914). 



6' R. Kuhn, G. Quadbeck, and E. Rohm, Ann. Chem. Justus Liebigs 565, 1 (1949). 



^°M. R. Stetten and D. Stetten, Jr., J. Biol. Chem. 164, 85 (1946). 



71 R. C. Anderson and E. S. Wallis, J. Am. Chem. Soc. 70, 2931 (1948). 



" T. Posternak, Helv. Chim. Acta 33, 1597 (1950). 



"T. Posternak, Helv. Chim. Acta 35, 50 (1952). 



''* S. J. Angyal and C. G. Macdonald, /. Chem. Soc. 1952, 686. 



