A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement.

BACKGROUND: α-Methylene cycloalkanones are considered of interest because of their biological activity. Herein, in this paper the synthesis of (±) HomoSarkomycine Esters was described and characterized. METHODS: Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine Esters could be synthesized by smoothly Johnson-Claisen rearrangement. RESULTS: A small library of target compounds was prepared under optimized reaction conditions in moderate yields. The reaction mechanism and the DFT study have been investigated. CONCLUSION: This methodology provides ready access to 2-hydroxymethyl-2-cyclopentenone 1a which can be served as the raw materials of the synthesis of (±) HomoSarkomycine Ester.