Asymmetric Total Synthesis of Eremophilanolide Sesquiterpene Xylareremophil and Its Congeners
The first asymmetric, protecting group free total synthesis of eremophilanolide sesquiterpenes, xylareremophil (<b>1</b>), 2α,3α-epoxymairetolide A (<b>2</b>), and 2,3-<i>seco</i>-2,3-olide-1-deoxygenmairetolide F (<b>3</b>), is concisely achieved with a longest linear route of five to eight steps, starting from the known (5<i>S</i>)-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.
Authors
- Huibin Wang (ORCID: https://orcid.org/0000-0002-0020-7197)
- Chun‐An Fan (ORCID: https://orcid.org/0000-0003-4837-3394)
- Yu-Han Yang
- Xian‐He Zhao (ORCID: https://orcid.org/0000-0002-1562-4292)
- Xian‐Tao An (ORCID: https://orcid.org/0009-0008-9452-2913)
- Le-Le Meng
- Xinyu Liu (ORCID: https://orcid.org/0000-0002-0564-7167)
- Junyi Zhou (ORCID: https://orcid.org/0009-0006-7520-0404)
- Tian-Jie Ge
Institutions
- State Key Laboratory of Chemical Engineering (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00028
- Citations
- 1
- Primary Topic
- Plant Toxicity and Pharmacological Properties
- Type
- article
- Field-Weighted Citation Impact
- 0.81
Funders
- National Natural Science Foundation of China
- Higher Education Discipline Innovation Project
- National Key Research and Development Program of China
- Science and Technology Program of Gansu Province