Syringin (<b>1</b>), a natural bioactive glucoside isolated from the root of <i>Acanthopanax senticosus</i> (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (<b>1</b>), along with its natural analogues <b>2</b>-<b>12</b>, from a common starting material, syringaldehyde (<b>13</b>), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds <b>1</b>-<b>5</b>, <b>7</b>, and <b>9</b> exhibited different levels of anti-inflammatory activity.