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

Sanjay Kumar 1
Sanjay Kumar
, 
Yoshitaka Koseki 1
Yoshitaka Koseki
, 
Takaaki Kamishima 2
Takaaki Kamishima
, 
Hitoshi Kasai 1
Hitoshi Kasai
1 Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai, Japan
2 East Tokyo Laboratory, Genesis Research Institute, Ichikawa, Chiba, Japan
10.1016/j.mencom.2024.06.019
Published 2024-06-19
Communication , Volume 34, Issue 4, 528-530
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Kumar S. et al. A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 528-530.
GOST all authors (up to 50) Copy
Kumar S., Koseki Y., Kamishima T., Kasai H. A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 528-530.
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TY - JOUR
DO - 10.1016/j.mencom.2024.06.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.019
TI - A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose
T2 - Mendeleev Communications
AU - Kumar, Sanjay
AU - Koseki, Yoshitaka
AU - Kamishima, Takaaki
AU - Kasai, Hitoshi
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 528-530
IS - 4
VL - 34
ER -
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@article{2024_Kumar,
author = {Sanjay Kumar and Yoshitaka Koseki and Takaaki Kamishima and Hitoshi Kasai},
title = {A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.019},
number = {4},
pages = {528--530},
doi = {10.1016/j.mencom.2024.06.019}
}
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Kumar, Sanjay, et al. “A concise synthesis of methyl dihydrojasmonate and methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from D-glucose.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 528-530. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.019.

Keywords

cyclopentadienone
D-glucose
fragrance
hedione
Johnson–Claisen rearrangement.
methyl dihydrojasmonate

Abstract

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.

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