A Total Synthesis of the Racemic Sesquiterpene Parvifoline

Abstract

A total synthesis of the sesquiterpene (±)-parvifoline 1 from the symmetrical naphthalene 4 is reported. The key step of the synthesis was a Stork−Landesman two-carbon ring expansion of β-tetralone 5, which affords 9a with the complete framework of the target. Although many reactions are involved in the sequence, the whole synthesis can be executed in only five synthetic operations and in ≈18% overall yield.