An efficient synthesis of ECH, epoxyquinols A and B, and two bioactive analogs EqM and RKTS-33 has been completed starting from (−)-shikimic acid. Rapid establishment of the desired epoxyquinol core is facilitated through a key allylic oxidation with high stereoselectivity, which is achieved by fine tuning the cyclohexene substrate structure and reaction conditions.
G. Luo, Y. Jia, Y. Hu, F. Wu, M. Wang and X. Chen, Org. Biomol. Chem., 2022, 20, 4608 DOI: 10.1039/D2OB00559J
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