Synthesis of cyclopropane-annulated conduritol derivatives: norcaran-2,3,4,5-tetraoles

Norcaran-2,3,4,5-tetraoles were synthesized starting from methyl 1,3,5-cycloheptatriene-7-carboxylate in several steps. Norcaradiene endoperoxide is the key component; it was obtained by photooxygenation of methyl 1,3,5-cycloheptatriene-7-carboxylate. The other oxygen functionalities are introduced through epoxide ring opening and OsO4-hydroxylation reactions.

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