Neolignan skeletons and benzodioxanes through chiral aryl alkyl ether formation

Several chiral neolignan skeletons and a benzodioxane were prepared from a tartrate derivative with the crucial chiral aryl alkyl ether formation bein g accomplished with cesium phenolate and 18-crown-6. These compounds have g reater than 96% enantiomeric excess, and this work represents the first suc cessful synthetic preparation of optically active 8-O-4' type neolignan ske letons. The chiral aryl alkyl ethers were also synthesized from several pro tected carbohydrates, which can serve as chiral auxiliaries for a wide vari ety or target molecules.