Novel stereodivergent total syntheses of all the seven stereoisomers of (−)‐shikimic acid (−)‐SA 1 have been systematically performed. (+)‐ent‐SA ent‐1 was synthesized from (−)‐SA 1 via 9 steps in 31 % overall yield; (−)‐3‐epi‐SA 2 was synthesized from (−)‐SA 1 via 5 steps in 66 % overall yield; (+)‐3‐epi‐ent‐SA ent‐2 was synthesized from (−)‐SA 1 via 7 steps in 43 % overall yield; (−)‐4‐epi‐SA 3 was synthesized from (−)‐SA 1 via 11 steps in 32 % overall yield; (+)‐4‐epi‐ent‐SA ent‐3 was synthesized from (−)‐SA 1 via 7 steps in 42 % overall yield; (−)‐5‐epi‐SA 4 was synthesized from (−)‐SA 1 via 6 steps in 56 % overall yield; and (+)‐5‐epi‐ent‐SA ent‐4 was synthesized from (−)‐SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (−)‐SA 1 were further studied by two dimensional (2D) 1H NMR technique. (−)‐Shikimic acid (−)‐SA 1 is a naturally‐abundant product from Chinese star anise. All of the seven stereoisomers i. e. (+)‐ent‐SA ent‐1, (−)‐3‐epi‐SA 2, (+)‐3‐epi‐ent‐SA ent‐2, (−)‐4‐epi‐SA 3, (+)‐4‐epi‐ent‐SA ent‐3, (−)‐5‐epi‐SA 4 and (+)‐5‐epi‐ent‐SA ent‐4 have been systematically synthesized from (−)‐SA 1.