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Synthesis of ( ±)-rupestine A and ( ±)-rupestine J, structural reassignment of rupestine A via ECD analysis

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( ±)-rupestine A and ( ±)-rupestine J were prepared in a 13–14-step linear approach. This strategy started from 3-bromo-6-methylpicolinonitrile employing Krapcho decarboxylation, Suzuki cross-coupling, RCM reaction as key steps. The structure of rupestine A was reassigned via analyzing all enantiomers with electronic circular dichroism (ECD) spectroscopy and was further proved by synthesis of rupestine J.

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This work was financially supported by West Light Foundation of the Chinese Academy of Sciences (No. 2016-QNXZ-B-6) and Scientific Research Program of the Higher Education Institution of Xinjiang (XJEDU2019Y044).

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Correspondence to Haji Akber Aisa.

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Aibibula, P., Yusuf, A., Zhao, J. et al. Synthesis of ( ±)-rupestine A and ( ±)-rupestine J, structural reassignment of rupestine A via ECD analysis. Chem. Pap. 75, 5599–5603 (2021).

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