A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A |
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| Authors: | Chaofan Huang Fuchun Shi Yifan Cui Can Li Jie Lin Qi Liu Anni Qin Huanan Wang Guolin Wu Penglin Wu Junzhe Xiao Haibo Xu Yuan Yuan Yizhan Zhai Wei-Feng Zheng Yangguangyan Zheng Biao Yu Shengming Ma |
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| Institution: | Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433 P. R. China ; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 P. R. China, |
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| Abstract: | A palladium-catalyzed C–O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional groups are tolerated and the synthetic utility of this method has been demonstrated through a series of transformations of the allene moiety. By applying this reaction as the key step, the total syntheses of naturally occurring allenic aromatic ethers, eucalyptene and terricollene A (first synthesis; 4.5 g gram scale), have been accomplished.A palladium-catalyzed C–O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. |
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