Abstract
The results are reported of the interaction of the trans,trans-germacradienolide hanphyllin with m-chloroperbenzoic acid and with 50% sulfuric acid. This leads to a cyclization reaction with the formation of eudesmanolides: 1β-hydroxy-3-oxo-1,4,5,7α(H),6β(H)-eudesm-11(13)-en-6,12-olide, ridentin B, and 3β-hydroxy-5,7α(H),6β(H)-eudesma-4(15),11(13)-dien-6,12-olide; and also products of the opening of the lactone ring as a consequence of transesterification. The structures of the compounds obtained are discussed on the basis of spectral results (IR, PMR, and mass spectra) and of x-ray structural analysis.
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Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 508–517, September–October, 1992.
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Adekenov, S.M., Gafurov, N.M., Turdybekov, K.M. et al. Transannular cyclization of the E,E-germacradienolide hanphyllin. Chem Nat Compd 28, 444–451 (1992). https://doi.org/10.1007/BF00630647
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DOI: https://doi.org/10.1007/BF00630647