The first total synthesis of three (+)-podophyllic aldehydes was achieved in a highly enantiocontrolled manner. Key steps include the organocatalyzed highly enantioselective cyclopropanation and Lewis acid-mediated chiral transfer ring expansion with excellent level of stereoinduction. This method can alternatively provide (+)- and (-)-podophyllic aldehydes by switching the organocatalyst in the asymmetric cyclopropanation.