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The asymmetric synthesis of the new lignan cubebin dimethyl ether was accomplished in eight steps with an overall yield of 40 %. In addition, the known lignans (+)-hinokinin and (+)-dihydrocubebin were synthesized by this route. Our approach involves the highly diastereoselective and enantioselective (de ≥ 98%, ee ≥ 98%) construction of a trans-substituted 2,3- dibenzylbutyrolactone through an asymmetric Michael addition of an enantiopure lithiated aminonitrile to 5H-furan-2-one.

Asymmetric Synthesis of (+)-Hinokinin, (+)-Dihydrocubebin and Cubebin Dimethyl Ether, a New Lignan from Phyllanthus niruri