S. Kumar, Y. Koseki, T. Kamishima, H. Kasai, “A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose”, Mendeleev Commun., 34:4 (2024), 528

Communications

A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose

S. Kumar^a, Y. Koseki^a, T. Kamishima^b, H. Kasai^a

^a Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai, Japan
^b East Tokyo Laboratory, Genesis Research Institute, Ichikawa, Chiba, Japan

Аннотация: Methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate were synthesized from 4-hydroxy-2-(hydroxymethyl)cyclopentenone, which, in turn, was obtained from D-glucose. The conditions for the key step, the Johnson–Claisen rearrangement, were optimized to get the maximum yield of the intermediate methyl 2-[2-methylene-3-oxo-5-(triisopropylsilyloxy)-cyclopentyl]acetate.

Ключевые слова: fragrance, D-glucose, hedione, methyl dihydrojasmonate, cyclopentadienone, Johnson–Claisen rearrangement.

Язык публикации: английский

DOI: 10.1016/j.mencom.2024.06.019

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		Supplementary_data_1.pdf	1.3 Mb