Synthesis of Mono-O-alkylated Homooxacalix[3]arene and a Protection-Deprotection Strategy for Homooxacalix[3]arene.

The regioselective synthesis of mono-O-alkylated homooxacalix[3]arene is accomplished for the first time. The synthetic route relies on two key steps: (i) a facile protection of two OH groups at the lower rim of the homooxacalix[3]arene and (ii) the deprotection of 9-anthrylmethyl groups via the Pd/C-catalyzed hydrogenation under atmospheric hydrogen. An efficient protection-deprotection strategy for the functionalization of homooxacalix[3]arene is presented.