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Synthesis of functional allyl-α-tetrahydropyrones from cyrene

Yuliya Aleksandrovna Khalilova 1
Yuliya Aleksandrovna Khalilova
, 
Liliya Khalitovna Faizullina 1
Liliya Khalitovna Faizullina
, 
Shamil Mubarakovich Salikhov 1
Shamil Mubarakovich Salikhov
, 
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
1 Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2024.06.016
Published 2024-06-19
Communication , Volume 34, Issue 4, 521-522
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Khalilova Y. A. et al. Synthesis of functional allyl-α-tetrahydropyrones from cyrene // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 521-522.
GOST all authors (up to 50) Copy
Khalilova Y. A., Faizullina L. K., Salikhov S. M., Valeev F. A. Synthesis of functional allyl-α-tetrahydropyrones from cyrene // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 521-522.
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TY - JOUR
DO - 10.1016/j.mencom.2024.06.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.016
TI - Synthesis of functional allyl-α-tetrahydropyrones from cyrene
T2 - Mendeleev Communications
AU - Khalilova, Yuliya Aleksandrovna
AU - Faizullina, Liliya Khalitovna
AU - Salikhov, Shamil Mubarakovich
AU - Valeev, Farid Abdullovich
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 521-522
IS - 4
VL - 34
ER -
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@article{2024_Khalilova,
author = {Yuliya Aleksandrovna Khalilova and Liliya Khalitovna Faizullina and Shamil Mubarakovich Salikhov and Farid Abdullovich Valeev},
title = {Synthesis of functional allyl-α-tetrahydropyrones from cyrene},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.016},
number = {4},
pages = {521--522},
doi = {10.1016/j.mencom.2024.06.016}
}
MLA
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Khalilova, Yuliya Aleksandrovna, et al. “Synthesis of functional allyl-α-tetrahydropyrones from cyrene.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 521-522. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.016.

Keywords

1
2-addition reaction
asperlin
cyrene
methylthiomethyl ethers.
tetrahydropyrans
α-tetrahydropyrones

Abstract

Addition of allylzinc to cyrene affords diastereomeric 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols. Opening of their 1,6-anhydro bridge with Ac2O followed by selective deacetylation of the resulting tertiary and acetal acetates yields diastereomeric 2-acetoxymethyl-5-allyl-tetrahydro- pyran-5,6-diols whose oxidation by the action of DMSO-Ac2O system is accompanied by etherification of tertiary hydroxy groups leading to methylthiomethoxy pyrone derivatives. The opening of 1,6-anhydro bridge in 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols with MeOH-HCl followed by oxidation with PCC gives individual (4S,6S)- 1-allyl-6-methoxy-2,5-dioxabicyclo[2.2.2]octan-3-one.

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