A Preliminary Approach to Nonenolizable β,β-Tricarbonyls: Assembly of a Hyperevolutin Prototype1

This is the authors' abstract. We don't add key points for this paper.

A synthetic approach to the hyperevolutin A acylated phloroglucinol ring system is described. Thus, intramolecular allene-nitrile oxide cycloaddition of 10 was used to construct the bicyclic framework and vicinal quaternary centers in cycloadduct 20 in the key bond-forming step. Treatment of 20 with Raney nickel and hydrogen gas produced primary enamine 21 which contains a nonenolizable beta,beta-tricarbonyl group in latent form.