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Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin

Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
, 
Yuliya Aleksandrovna Khalilova 1
Yuliya Aleksandrovna Khalilova
, 
Marsel G. Yalalov 2
Marsel G. Yalalov
, 
Artur R Tagirov 3
Artur R Tagirov
, 
Shamil M Salikhov 1
Shamil M Salikhov
, 
El'za Makmunovna Minnibaeva 2
El'za Makmunovna Minnibaeva
, 
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
1 Ufa Federal Research Centre of the Russian Academy of Sciences, 450054 Ufa, Russian Federation
2 Institute of Chemistry and Protection in Emergency Situations, Ufa University of Science and Technology, 450076 Ufa, Russian Federation
3 Ufa State Petroleum Technical University, 450064 Ufa, Russian Federation
10.71267/mencom.7537
Published 2025-01-24
Communication , Volume 35, Issue 1, 57-59
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Faizullina L. K. et al. Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 57-59.
GOST all authors (up to 50) Copy
Faizullina L. K., Khalilova Y. A., Yalalov M. G., Tagirov A. R., Salikhov S. M., Minnibaeva E. M., Valeev F. A. Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 57-59.
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TY - JOUR
DO - 10.71267/mencom.7537
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7537
TI - Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin
T2 - Mendeleev Communications
AU - Faizullina, Liliya Khalitovna
AU - Khalilova, Yuliya Aleksandrovna
AU - Yalalov, Marsel G.
AU - Tagirov, Artur R
AU - Salikhov, Shamil M
AU - Minnibaeva, El'za Makmunovna
AU - Valeev, Farid Abdullovich
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 57-59
IS - 1
VL - 35
ER -
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@article{2025_Faizullina,
author = {Liliya Khalitovna Faizullina and Yuliya Aleksandrovna Khalilova and Marsel G. Yalalov and Artur R Tagirov and Shamil M Salikhov and El'za Makmunovna Minnibaeva and Farid Abdullovich Valeev},
title = {Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7537},
number = {1},
pages = {57--59},
doi = {10.71267/mencom.7537}
}
MLA
Cite this
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Faizullina, Liliya Khalitovna, et al. “Diels-Alder adduct of levoglucosenone and isoprene in the syntheses of the key synthon for loganin.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 57-59. https://mendcomm.colab.ws/publications/10.71267/mencom.7537.

Keywords

Diels–Alder adduct
levoglucosenone
loganin
oxidation.
periodate cleavage
Wagner vic-hydroxylation

Abstract

Based on the hemiketal obtained by the carbonyl eneketalization of the Diels-Alder adduct of levoglucosenone and isoprene with acetaldehyde, two methods have been suggested for incorporating the carboxy group of loganin at the pyran ring. The first method involved one-pot conversion employing ozonolytic cleavage of the double bond, ozonide reduction, in situ aldehyde oxidation and esterification. An alternative five-step sequential conversion of the ketal, with isolation and identification of intermediate compounds, involved ketalization, Wagner vic-hydroxylation of the double bond, periodate cleavage of diols, in situ oxidation of the aldehyde to an acid, and esterification.

Funders

Ministry of Education and Science of the Russian Federation
122031400259-1, 122031400282-9

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