Improved synthesis of 2,10-dioxatricyclo[4,4,4,0^1,6]tetradecanes

Abstract

Cyanoethylation of substituted cyclohexanones at low temperatures has been found to give markedly improved yields and regioselectivity over the usual conditions for the Michael reaction. This reaction greatly facilitated the preparation of the 2,10-dioxatricyclo[4,4,4,0^1.6]tetradecanes (1). Carbon-13 n.m.r. data are reported for several substituted ketone and acetal intermediates and for the tricyclic acetal product (1b).