Molecular diversity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis and sigmatropic shifts: a general and stereoselective route to novel spirocarbocyclics

摘要

A novel, general and stereoselective route to spiroannulated bicyclo[2.2.2]octenones and their transformation to spiroannulated bicyclo[3.3.0]- and bicyclo[4.2.0]octanes is described. Oxidative dearomatization of o-hydroxymethylphenols, cycloaddition of spiroepoxycyclohexadienones, ring-closing metathesis and photochemical sigmatropic 1,2- and 1,3-acyl shifts are the key features of our methodology. (C) 2014 Elsevier Ltd. All rights reserved.