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Updated: Jul 14, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Synthesis of +-dihydro-epi-deoxyarteannuin B
Gregory B Dudley1, Douglas A Engel, Ion Ghiviriga
1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu
Abstract:
The synthesis of (+)-dihydro-epi-deoxyarteannuin B (3) from (-)-isopulegol is described. Difficulties in the alkylation of menthone derivatives (e.g., 4a --> 6a) were overcome by using Noyori's zincate enolate method. Related problems with nucleophilic addition to the hindered menthone core of 6a were resolved by using either organocerium or acetylide nucleophiles. Finally, two alternative olefin metathesis approaches are reported for the final cyclization. This study provides insight into the reactivity and synthetic processing of the artemisinin sesquiterpenes.
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