Abstract
The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH 4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.
The first total synthesis of dilignan Boehmenan was achieved through eight steps from vanillin. Meanwhile, a study on ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.
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Acknowledgements
This work was supported by the National Natural Science Foundation of Shandong (No. ZR2010HM023), the Chinese Medicine Administration Bureau of Gansu Province (No.GZK-2011-62).
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XIA, Y., DAI, X., LIU, H. et al. First total synthesis of Boehmenan. J Chem Sci 126, 813–820 (2014). https://doi.org/10.1007/s12039-014-0599-7
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DOI: https://doi.org/10.1007/s12039-014-0599-7