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Total Synthesis of (-)-Steganacin via Stereocontrolled Atroposelective Intramolecular Mizoroki-Heck Reaction and
Shuxin Yang1, Qikun Yin1, Xuanyu Liu1
1School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai 264005, China.
Abstract:
(-)-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 IC50 = 0.50 μM.
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