No abstract

Several chiral neolignan skeletons and a benzodioxane were prepared from a tartrate derivative with the crucial chiral aryl alkyl ether formation being accomplished with cesium phenolate and 18-crown-6. These compounds have greater than 96 % enantiomeric excess, and this work represents the first successful synthetic preparation of optically active 8-O-4' type neolignan skeletons. The chiral aryl alkyl ethers were also synthesized from several protected carbohydrates, which can serve as chiral auxiliaries for a wide variety of target molecules.