Design, synthesis and application of spiro[4.5]cyclohexadienones via one-pot sequential p-hydroxybenzylation/oxidative dearomatization.

One-pot sequential p-hydroxybenzylation/oxidative dearomatization/spiroannulation has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones. This reaction proceeds through the p-hydroxybenzylation of 1,3-diketones with p-hydroxybenzyl alcohol via quinone methide formation followed by oxidative dearomatization/spiroannulation with suitable alcohols. The Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provided a broad array of highly diastereoselective C-3 alkylated spirocycles and cyclohepta[b]indoles depending upon the ring size of the fused cyclic ketones.