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Updated: Oct 2, 2025

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Synthesis of 9,11-Secosteroids Pinnisterol E, Glaciasterol B, and 6-Keto-aplidiasterol B
Yinlong Miao1, Xinghui Li2, Mengqing Zhang1
1Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China.
Abstract:
A 10-step gram-scale synthesis of 9,11-secosteroid pinnisterol E from the inexpensive ergosterol is reported. This synthesis features a series of highly selective redox transformations such as regioselective olefin hydrogenation (PtO2), acid-sensitive endoperoxide reduction (Al-Ni alloy, Zn), and regio- and diastereoselective dienone oxidation. The robustness of this strategy is clearly demonstrated through the formal synthesis of 11(9 → 7)abeo-steroid pleurocin B and the divergent synthesis of 9,11-secosteroids glaciasterol B and 6-keto-aplidiasterol B from the inexpensive cholesterol.
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