文摘
The first total synthesis of racemic naupliolide is accomplished from a known cyclic acetal in a total of 18 steps and includes a Simmons-Smith cyclopropanation of an allylic 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.