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

• DOI: 10.1016/j.tet.2014.12.033
• Publication Date: 2014-12-13T02:07:19Z
• Authors: Vishwakarma Singh; Beauty Das; Dnyandev B. Jarhad; Shaikh M. Mobin
• Keywords: Ring-Closing Metathesis

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.