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Updated: May 26, 2025
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Asymmetric Total Synthesis of Eremophilanolide Sesquiterpene Xylareremophil and Its Congeners
Hui-Bin Wang1, Tian-Jie Ge1, Xian-Tao An1
1State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Abstract:
The first asymmetric, protecting group free total synthesis of eremophilanolide sesquiterpenes, xylareremophil (1), 2α,3α-epoxymairetolide A (2), and 2,3-seco-2,3-olide-1-deoxygenmairetolide F (3), is concisely achieved with a longest linear route of five to eight steps, starting from the known (5S)-5,6-dimethyl-2-cyclohexenone as the chiral starting material. This synthetic approach mainly features an oxa-Pauson-Khand reaction of the highly functionalized chiral aldehyde precursor, forging a γ-butenolide-fused tricyclic core framework of eremophilanolides in a one-step manner. This study provides a novel strategic perspective for the divergent synthesis of the eremophilanolide sesquiterpenes.
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