Total Synthesis of (−)-Steganacin via Stereocontrolled Atroposelective Intramolecular Mizoroki-Heck Reaction and Evaluation of Biological Activity
(-)-Steganacin is a lignan with a unique dibenzocyclooctadiene lactone framework. Herein, we describe the total synthesis of (-)-steganacin and its congeners through a stereocontrolled atroposelective intramolecular Mizoroki-Heck reaction. The synthesis of (-)-steganacin was completed in 11 steps from commercial substrates with a 7% overall yield. Furthermore, the biological activities of (-)-steganacin and its synthetic analogues were evaluated. (-)-Steganacin exhibits potent antiproliferation activity against MDA-MB-468 breast cancer cells with IC<sub>50</sub> = 0.50 μM.
Authors
- Shuxin Yang
- Xuanyu Liu (ORCID: https://orcid.org/0000-0001-8916-9942)
- Yi Bi (ORCID: https://orcid.org/0000-0003-0879-0572)
- Qikun Yin (ORCID: https://orcid.org/0000-0002-4530-4089)
- Xianhe Fang
Institutions
- Yantai University (CN)
- Systèmes avancés de délivrance de principes actifs
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-04
- DOI
- https://doi.org/10.1021/acs.orglett.5c02711
- Citations
- 1
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Yantai University
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Taishan Scholar Project of Shandong Province
- Science and Technology Support Plan for Youth Innovation of Colleges and Universities of Shandong Province of China