Summary
Relative difficulty of saponifying an acetoxy group at C1 and ease of acylation of a hydroxy group in this position as compared with a hydroxy group C10 has been shown for alkaloids with a lycoctonine skeleton.
The anomalously easy saponification of a C1-acetoxy group in karakolidine acetates is due to the influence of the neighboring C13-hydroxy group.
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Literature cited
M. N. Sultankhodzhaev, M. S. Yunusov, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 199 (1973).
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Additional information
Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 381–383, May–June, 1975.
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Sultankhodzhaev, M.N., Yunusov, M.S. & Yunusov, S.Y. Stereochemical features of diterpene alkaloids in acylation and alkaline hydrolysis reactions. Chem Nat Compd 11, 392–394 (1975). https://doi.org/10.1007/BF00571216
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DOI: https://doi.org/10.1007/BF00571216