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Abstract
Synthesis of 2-acetoxy[5]helicene has been achieved by sequential double aromatic oxy-Cope rearrangement strategy. Combination of 1-methoxybicyclo[2.2.2]oct-5-en-2-one and p-bromophenylmagnesium bromide gave 3-bromophenanthrene through several steps including an aromatic oxy-Cope rearrangement as a key step. The second oxy-Cope rearrangement and the following transformation gave 2-acetoxy[5]helicene by similar procedure.
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