The alkaloid norfluorocurarine was reduced under various conditions to produce the novel bisindoline derivative 2,16-dihydro-19-oxo-C-dihydrotoxiferine and the previously known natural derivatives deoxydihydro-, deoxytetrahydro-, and tetrahydronorfluorocurarine. The structures of the synthesized compounds were identified using IR and UV spectroscopy; of newly produced 2,16-dihydro-19-oxoC-dihydrotoxiferine and deoxydihydronorfluorocurarine, also by x-ray structure analysis. Determination of the absolute configuration of N(α)-methylfluorocurarine chloride dihydrate by x-ray methods enabled the configuration of the 3S,7R,15S asymmetric centers in norfluorocurarine and 2S,3S,7R,15S in deoxydihydronorfluorocurarine to be determined. Also, the absolute configuration of 2,16-dihydro-19-oxoC-dihydrotoxiferine was determined as 2S,3S,7R,15R,16R in one part of the bisindoline and 3'S,7'R,15'S in the other.
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Acknowledgment
The work was financed by the Basic Research Program of KKRNT, Rep. Uzb., Grant FA-F3-T045 and the Foundation for Basic Research Support, Acad. Sci., Rep. Uzb., Grant FPFI3910.
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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 652–656, September–October, 2010.
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Yuldashev, P.K., Tashkhodzhaev, B., Turgunov, K.K. et al. Reduction products of the alkaloid norfluorocurarine. Chem Nat Compd 46, 774–778 (2010). https://doi.org/10.1007/s10600-010-9738-7
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DOI: https://doi.org/10.1007/s10600-010-9738-7