A novel and stereospecific synthesis of conduritol-E via cyclohexa-3,5-diene-1,2-diol

Conduritol-E was synthesized starting from cyclohexa-3,5-diene-1,2-diol $1$ in six steps. Acetylation of the diol $(1a)$ followed by bromination gave (2$\alpha/1\beta$,3$\beta$, 4$\beta$)-1,2-dibromo-2,3-diacetoxy- 5-cyclohexene $3$ as main product. $KMnO_4$-hydoxylation of the dibromide $3$ followed by acetylation, Zn-elimination and hydrolysis afforded conduritol-E $5a$.