Drimenic acid was synthesized in six steps from norambreinolide. Reaction of drimenic acid with oxalyl chloride produced iso-drimenic acid chloride, which reacted with heterocyclic amines (2-aminopyrimidine, 2-aminopyrazine, 4-aminopyrimidine, N-aminocarbazole, and 3-amino-1,2,4-triazole) to form amides of iso-drimenic and albicanic acids. The structures of the amides were elucidated by spectral methods and an X-ray structure analysis.
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 386–390.
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Aricu, A.N., Kuchkova, K.I., Secara, E.S. et al. Synthesis and Structure of Drimane Sesquiterpenoids Containing Pyrimidine, Pyrazine, 1,2,4-triazole, and Carbazole Rings. Chem Nat Compd 54, 455–460 (2018). https://doi.org/10.1007/s10600-018-2378-z
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DOI: https://doi.org/10.1007/s10600-018-2378-z