Iotrochamide B is the first cinnamoyl amino acid reported from the marine sponge Iotrochota sp. The total synthesis of the marine indole alkaloid iotrochamide B was achieved by condensation of 6-bromo-L-tryptophan (3) and (Z)-2-methoxy-3-phenylacrylic acid (6). The key step was the synthesis of 6-bromo-L-tryptophan ((S)-3) from racemic N-acetyltryptophan by optical resolution using (S)-(–)-1-phenylethylamine. This work provides an efficient method for future synthesis of iotrochamide B derivatives.
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This work was supported by Scientific Research Fund of Xinxiang Medical University grants [2013QN121].
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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2019, pp. 428–430.
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Wang, S.Y., Zhao, J. & Que, H.D. Synthesis of the Natural Product Iotrochamide B. Chem Nat Compd 55, 499–501 (2019). https://doi.org/10.1007/s10600-019-02724-5
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DOI: https://doi.org/10.1007/s10600-019-02724-5