Studies Toward the Total Synthesis of Gliomasolide C

ABSTRACT This article describes the synthetic studies of gliomasolide C utilizing D‐mannitol as a chiral pool material. Julia–Kocienski olefination and Noyori asymmetric reduction were employed to synthesize an advanced intermediate, from which two key precursors for ring‐closing metathesis and intramolecular Horner–Wadsworth–Emmons olefination were prepared. Unfortunately, both ring‐closing metathesis and Horner–Wadsworth–Emmons olefination were unsuccessful in constructing the desired 14‐membered ( E )‐ α,β ‐macrolactone core.