A Streamlined Approach for Synthesizing Methyl Dihydrojasmonate and Methyl (5-Methylidene-4-Oxocyclopent-2-En-1-Yl)Acetate from D-Glucose

The methyl dihydrojasmonate (Hedione®) and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate were synthesized from 4-hydroxy-2-(hydroxymethyl)cyclopentenone, which was obtainbed from D-glucose. The reaction condition of the key reaction, Johnson-Claisen rearangement, was optimized to get maximum yield of an intermediate, methyl 2-(2-methylene-3-oxo-5-((triisopropylsilyl)oxy)cyclopentyl)acetate. Common internmedite was used for the synthesis of both dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate.