Catechol monoether synthesis

Abstract

In earlier work we have demonstrated efficient methods for appending benzene rings, phenols, and pyridines onto a-methylene ketones.1 The yields for these processes have been uniformly high, suggesting that the approach will be useful in total synthesis. The extension of this methodology to the synthesis of catechol monoethers will now be described.

Hydroxyquinone annelation

“…R f = 0.41 (25% ethyl acetatdhexanes); lH n.m.r. (300MHz, CDC13) 5.83 (s, l H ) , 3 which was the desired hydroxyquinone. The success of the reaction in the case of (la)-( Id) is likely to be a consequence of the enforced proximity of the ketone enolate and aldehyde groups (cf.…”