Abstract
AbstractA C2‐symmetric 7,8‐dioxa[6]helicene‐2,13‐diol was synthesized from readily available 2,7‐dihydroxynaphthalene on a gram scale. A high‐yielding synthetic strategy for the regioselective hydroxymethylation at the sterically most hindered C1 position of diol analogues was investigated. The dioxa[6]helicene backbone with configurationally stable helical enantiomers was synthesized, and these enantiomers were separated by HPLC on a chiral stationary phase. We also observed an unexpected domino Prins reaction. This is the first report of a domino Prins reaction occurring on a helicene. Along with the high‐yielding regioselective functionalization of dioxa[6]helicene analogues, the synthesis of a few cis‐7a,14c‐dihydro‐functionalized helicenoid diols substituted at the sterically most hindered C1 and C14 positions in their racemic forms was explored.
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