Quercitol and Z-Viburnitol

Sixteen pentahydroxycyclohexanes are predicted on the basis of stereochemical theory. The configuration of d-quercitol was limited to that shown below by nitric acid oxidation to galactaric (mucic) acid (8 ) and by alkaline permanganate oxidation to 3-deoxy-D-galactaric acid (metasaccharinic acid) (83), This same acid was obtained from Z-viburnitol (58), Hence, the arrangement of hydroxyl groups on carbon atoms 2, 5, and 6 of d-quercitol and Z-viburnitol must be the same. Another series of reactions also led to identical compounds from these two deoxyinositols (53), It was found that Acetobacter suboxydans catalyzed the oxidation of Z-viburnitol to a deoxy- 

The configuration of conduritol, and incidentally those of aZZo-inositol, mwco-inositol, and dihydroconduritol, was elucidated in 1939 by Dangschat and Fischer (6 ), who applied the acetonation-oxidation technique previously used so successfully on quinic and shikimic acids. The steps utilized were as follows  

however, conduritol was first acetylated then the following results were obtained  

With the establishment of the configuration of m2/o-inosose-2 (see p. 281), Posternak (66) was able to proceed with the configuration of mytilitol, and a number of synthetic products, isomytilitol, hydroxymytilitol, and hydroxyisomytilitol, through the following series of reactions  

Since hydrogenation of both the epoxide derivative of m2/o-inosose-2 

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