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Total Synthesis of Gracilamine
Authors:Yingbo Shi  Baochao Yang  Shujun Cai  Prof?Dr Shuanhu Gao
Institution:1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062 (China);2. Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
Abstract:The total synthesis of gracilamine, a pentacyclic Amaryllidaceae alkaloid, was achieved from simple building blocks. The synthesis features a mild photo‐Nazarov reaction, intramolecular 1,4‐addition, and an intramolecular Mannich reaction. This approach not only confirms the C6 stereochemistry of natural gracilamine, and also provides a novel solution to prepare its derivatives and structurally related natural products.
Keywords:cross coupling  cyclization  natural products  photochemistry  total synthesis
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