Synthetic studies toward anisatin: A formal synthesis of (±)-8-deoxyanisatin

Abstract

equations presented An efficient strategy to construct the congested C-7a quaternary chiral center of anisatin was developed, by way of an Eschenmoser-Claisen rearrangement. Conversion of the resultant amide to Kende's ε-lactone intermediate 3 in four steps completed a concise formal synthesis of (±)-8-deoxyanisatin (2).