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Published on: November 9, 2019
Total synthesis of (-)-orthodiffenes A and C
1State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. junliu@rcees.ac.cn
Abstract:
The efficient and concise synthesis of (-)-orthodiffenes A and C has been accomplished for the first time in eight steps from readily available chiral synthons, D-mannose and D-ethyl lactate. Our work confirmed the complete structure of orthodiffenes A and C, including their absolute stereochemistry. The key steps of our total synthesis involved cis-fused tetrahydrofuran cyclization, one-pot deprotection-lactonization, and intramolecular benzoyl migration according to a biosynthetic hypothesis of orthodiffenes.
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