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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.

Neolignan Skeletons and Benzodioxanes Through Chiral Aryl Alkyl Ether Formation