Studies on epoxides-V. Reactions with 5,6-epoxy-eudesman-8β,12-olides

P. Vita-Finzi*, Y. Kashman, E. Glotter, D. Lavie

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The acid catalysed opening of the epoxide ring in several 5,6-epoxy-eudesman-8β,12-olides has been analysed. Treatment of the α-oriented epoxides XI and XIVb with HBr results in the formation of the diols XIX and XXI, whereas the β-epoxide XIII yields the expected trans diequatorial bromohydrin XXVId. The above and some other related reactions of eudesm-5-en-8β,12-olides with osmium tetroxide are described. An internal displacement of the epoxide ring in the epoxy-lactone XVI to yield the hydroxy-lactone XXVII takes place under mild alkaline conditions.

Original languageEnglish
Pages (from-to)5847-5859
Number of pages13
Issue number17
StatePublished - 1968
Externally publishedYes


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