Total Synthesis of Novel Oxylipins: Plasmodiophorols A, C, and Epimers
Year: 2026
Type: article
Abstract: In 2021, novel oxylipins plasmodiophorol A–C were identified as products of the hydroperoxide bicyclase activity of CYP50918A1 from Plasmodiophora brassicae (Rhizaria, SAR). Here, we report the first total syntheses of plasmodiophorol A and C in 12 and 13 steps, respectively, starting from chiral tetrahydro‐1H‐cyclopentafuranone. Key transformations included enzymatic desymmetrization, epimerization, and diastereoselective Grignard addition. Notably, during the synthesis of plasmodiophorol C, we also generated and structurally characterized a previously unknown compound. These synthetic routes provide reliable access to plasmodiophorols A and C, offering valuable standards for probing their biosynthetic pathways and facilitating their identification in marine biomasses. This work lays the foundation for further chemical and biological studies of these unique oxylipins.
DOI: 10.1002/ejoc.70449
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
OpenAlex ID: W7154741568