Abstract

The superacidic low-temperature cyclization of terpenols and their acetates by fluorosulfonic acid represents a highly efficient chemo- and structurally selective and stereospecific process. Homoallylic alcohols (α-isomers of cycloterpenols) are the products of cyclization of terpenols; the configuration of the hydroxymethyl group in the products is predetermined by the configuration of the allylic double bond in aliphatic or partially cyclized precursors. The cyclization of terpenyl acetates yields monoacetates of fully cyclized diastereomeric primary-tertiary γ-diols. Their stereochemistry also depends on the configuration of the allylic double bond in the starting substrates.

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