1-epi-Gallicin (10), a modified germacranolide, has been prepared from gallicin (12). A biogenetic-type cyclization of (10) afforded 1 α-hydroxy-trans-eudesmanolides. The mechanism and the stereospecificity of the reaction are discussed in terms of a preferred reacting conformation. The possible biogenetic significance of the process is outlined.
A. G. González, A. Galindo, H. Mansilla and A. Gutiérrez, J. Chem. Soc., Perkin Trans. 1, 1982, 881 DOI: 10.1039/P19820000881
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