Year: 2026
Type: article
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.
Source: The Journal of Organic Chemistry
Institution: Mahidol University
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Award: G880975939
OpenAlex ID: W7151492083