Reduced derivatives of 2,3-seco-28-oxo-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid and its cyclic anhydride were prepared. Reduction of the starting 2,3-secodicarboxylic acid by NaBH4–I2 produced the 2,3-seco-2,3-dihydroxy derivative. Reaction of the starting anhydride with LiAlH4 gave the 2,3-seco2,3,19β,28-tetrahydroxy derivative. Cyclization using acidic reagents of the 2,3-seco-2,3-hydroxy- and 2,3seco-2,3,19β,28-tetrahydroxy derivatives gave the corresponding cyclic ethers containing an oxepane ring. The anhydride ring was reduced by NaBH4 to the corresponding ε-lactone, the structure of which was confirmed by an x-ray crystal structure.
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Notes
The PMR spectrum of 9 recorded in DMSO-d6 also showed resonances for OH groups as a broad triplet at 3.98 (J ~ 4, 28-OH) and a broad doublet at 4.15 (J = 4.5, 19-OH).
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Acknowledgment
The work was supported financially by the RAS Presidium Basic Research Program “Development of Methods for Preparing Chemical Compounds and Creating New Materials”.
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 218–223, March–April, 2011
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Shernyukov, A.V., Mainagashev, I.Y., Korchagina, D.V. et al. Reduction of 2,3-Seco-28-oxo-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid and its cyclic anhydride. Chem Nat Compd 47, 237–242 (2011). https://doi.org/10.1007/s10600-011-9891-7
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DOI: https://doi.org/10.1007/s10600-011-9891-7