Bioinspired Collective Synthesis of Gymnothelignans I, F, K, and L
Issued Date
2026-04-17
Resource Type
ISSN
00223263
eISSN
15206904
Scopus ID
2-s2.0-105036878890
Journal Title
Journal of Organic Chemistry
Volume
91
Issue
15
Start Page
5334
End Page
5343
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry Vol.91 No.15 (2026) , 5334-5343
Suggested Citation
Chumsri N., Chualong K., Chairoungdua A., Kuhakarn C., Leowanawat P., Reutrakul V., Soorukram D. Bioinspired Collective Synthesis of Gymnothelignans I, F, K, and L. Journal of Organic Chemistry Vol.91 No.15 (2026) , 5334-5343. 5343. doi:10.1021/acs.joc.5c03261 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/116497
Title
Bioinspired Collective Synthesis of Gymnothelignans I, F, K, and L
Author's Affiliation
Corresponding Author(s)
Other Contributor(s)
Abstract
We report a collective stereoselective synthesis of gymnothelignan members, i.e., gymnothelignans I, F, K, and L, based on their proposed biosynthetic pathways. A chiral eupomatilone skeleton was employed as a key common intermediate. Reduction of a carbonyl moiety of eupomatilone readily gave gymnothelignan I, which was smoothly converted to the corresponding oxocarbenium ion upon treatment with an acid. Subsequent intermolecular and intramolecular nucleophilic additions of respective nucleophiles to the oxocarbenium ion provided gymnothelignans F, K, and L. This work provides information to support the plausible biosynthetic pathway of these structurally unique lignans.