Conduritol configuration

The latter on ammonolysis gave the free pentol, m.p- OS . The meso(1245/3) configuration was established by correlation with 2,3-an-hydro-epf-inositol (115), correlated in turn with conduritol-F (113), and DL(1235/46)-inosamine. 

The tetrol configurations meso(1234) and weso(14/23), (62 and 60), were established by chemical correlations with mcso-epi-inositol (18) and meso-conduritol-A (32), both of previously known configuration. The absolute configurations of the eight active orfAo-tetrols were established by indirect chemical correlations with (—)-t 6o-quercitol (30), (-l-)-pinitol (66), (—)-inositol (93), and (— )-quebrachitol (93, 2-methyl ether), all of known, absolute configuration. 

Catalytic oxidation of all six conduritols has been studied. In each case, an allylic hydroxyl group was oxidized, regardless of the configuration or conformation, giving a trihydroxycyclohexenone (122). ... 

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 ... 

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