Facile total synthesis of (±)-α-herbertenol, (±)-1,4-cuparenediol and (±)-cuparene- 1,4-quinone

Abstract

The total syntheses of the bicyclic sesquiterpene phenols (′)-α-herbertenol (1) and (′)-1,4-cuparenediol (2) have been successfully accomplished involving copper-catalysed conjugate addition of Grignard reagents to unsaturated dinitriles and α,α-dimethylation of primary esters as key reactions. Oxidation of 2 afforded the sesquiterpene quinone 3.