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Superacidic low temperature cyclisation of bicyclogeranylfarnesoic acid methyl esters (1 and 2) exhibiting the 13Z-configuration afforded cheilanthane and rearranged cheilanthane terpenoids as main products, along with scalarane compounds. In particular, 14-epi-cheilanthanic ester (6) was obtained together with 18-epi-scalaranic ester (5) by cyclisation of 13Z,17Z-bicyclogeranylfarnesoic acid methyl...
The superacidic cyclization of aliphatic and partially cyclized C 10 C 20 terpenylphenylsulfones proceeds structure-selectively and stereospecifically, affording α- or mixtures of α- and γ-isomers of completely cyclized terpenylphenylsulfones. The configuration of the phenylsulfonylmethylene group in the cyclized products is predetermined by the configuration of the allylic...
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