Synthesis of (S)-ktedonoketone

Abstract

The first total synthesis of (S)-ktedonoketone has been accomplished in 16% overall yield from (R)-2-hydroxybutyric acid by an eight-step sequence that features a highly diastereoselective methallylation of a chiral dioxolanone and a nucleophilic addition of α-lithiostyrene to a Weinreb’s amide intermediate followed by ring-closing metathesis of the resulting enone to construct an α,β-disubstituted cyclopentenone ring system. The sign of specific rotation of synthetic (S)-ktedonoketone was opposite to that reported for the natural product.