To prepare a tetrapropoxy-p-tert-butyldicalix[4]arene (5), we began by lithiating tetramethoxy-p-tert-butylcalix[4]arene (1) and treated the intermediate 2 with 1,6-dibromohexane to create the octamethoxy dicalix[4]arene 3. Demethylation of 3 at the lower rim with hydrogen iodide (generated from decomposition of cyclohexyl iodide) yielded the octahydroxy dicalix[4]arene 4. Compound 4 was subsequently fully propylated to give the octapropoxy species 5, which has both calix[4]arene units in the cone conformation. Transformation of the upper-rim tert-butyl groups of 5 to alkylammonium groups could result in a dicalix[4]arene that has the potential to bind in the major groove of DNA.

Synthesis of dicalix[4]arenes with methylene-bridge flexible linkers

249th National Meeting (2015)

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