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CC BY 4.0 · Pharmaceutical Fronts 2021; 03(03): e113-e118
DOI: 10.1055/s-0041-1740241
Original Article

Asymmetric Synthesis of 1,2-Limonene Epoxides by Jacobsen Epoxidation

Zi-Yi Huang‡   #
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
2   School of Pharmacy, Fudan University, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Min-Ru Jiao‡   #
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Xiu Gu
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
4   School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
,
Zi-Ran Zhai
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
5   School of Engineering, China Pharmaceutical University, Nanjing, People's Republic of China
,
Jian-Qi Li
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Qing-Wei Zhang
1   Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
3   Shanghai Engineering Research Center of Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
› Institutsangaben Funding Information This work was financially supported by the National Science and Technology Major Project (Grant No. 2018ZX09711002-002-009), the National Natural Science Foundation of China (Grant No. 81703358), and Science and Technology Commission of Shanghai Municipality (Grant No. 17431903900, 18QB1404200, and 21S11908000).
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Abstract

This study reported an asymmetric synthesis of 1,2-limonene epoxides. The absolute stereochemistry was controlled by a Jacobsen epoxidation of cis-1,2-limonene epoxide (with diastereomeric excess of 98%) and trans-1,2-limonene epoxide (with diastereomeric excess of 94%), which could be used as important raw materials for the preparation of related cannabinoid drugs.

Keywords

Jacobsen epoxidation - 1,2 limonene epoxides - asymmetric synthesis

# These authors contributed equally to this work.




Publikationsverlauf

Eingereicht: 29. November 2020

Angenommen: 29. September 2021

Artikel online veröffentlicht:
20. Dezember 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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