The Total Synthesis of (±)‐Naupliolide: A Tetracyclic Sesquiterpene Lactone

Abstract The first total synthesis of (±)‐naupliolide has been achieved. The synthetic method includes a Simmons–Smith cyclopropanation of an allyl alcohol, diastereoselective cleavage of a benzylidene acetal group, radical cyclization of an aldehyde with a cyclopropane ring, and construction of an eight‐membered ring by ring‐closing metathesis.