The first total synthesis of the natural nematicidal cyclic lipodepsipeptide ophiotine via a convergent strategy that involved both solid-phase peptide synthesis and liquid phase chemistry is reported. The pre-made dipeptide building block was synthesized in the liquid phase, which was then assembled into the peptide backbone through standard Fmoc chemistry on solid support. After cleavage from the resin, the linear peptide was cyclized by the liquid phase macrocyclization and the side chain deprotection successively, which led to the crude ophiotine. Finally, the crude product was purified by preparative reverse-phase highperformance liquid chromatography, and its structure was confirmed by NMR and HR-ESI-MS.
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Acknowledgment
We are grateful to the National Natural Science Foundation of China (21402235) and the Instrumental Analysis Center of our university for NMR spectroscopic and mass spectrometric analysis.
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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2020, pp. 756–759.
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Wang, J., Liu, C., Hu, HG. et al. Total Synthesis of Cyclic Lipodepsipeptide Ophiotine. Chem Nat Compd 56, 883–887 (2020). https://doi.org/10.1007/s10600-020-03175-z
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DOI: https://doi.org/10.1007/s10600-020-03175-z