Synthesis of the cyclophane tetramethoxyturriane: a derivative of the phenolic cyclophanes of Grevillea striata R. Br.

Abstract

The synthesis of 9,10,11,12,13,14,15,16,17,18,19,20,21,22-tetradecahydro-2,4,6,24-tetramethoxy-5,8-ethenobenzocycloeicosene (tetramethoxyturriane)(9) a derivative of the phenolic cyclophanes extracted from the wood of Grevillea striata R.Br., is reported. The key steps in this synthesis were the construction of the biphenyl linkage of the molecule using dihydro-oxazole chemistry and the closure of the macrocycle by oxidative coupling of a diacetylene.