Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides

F.J. Moreno-Dorado, Y.M.A.W. Lamers, G. Mironov, J.B.P.A. Wijnberg, Æ. de Groot

Research output: Contribution to journalArticleAcademicpeer-review

18 Citations (Scopus)


The chemistry of (+)-ledene and (-)-isoledene, both easily available from (+)-aromadendrene has been investigated. Reactions at the double bond of ledene take place preferably from the ß-side. Under acidic conditions its C7–C8 ß-epoxide and ß-diol preferably react via carbocations, which are initially formed at C8. Rearrangement takes place to compounds with cubebane and cadinane skeletons. The reaction pattern of isoledene and its a-epoxide, under acidic conditions, is governed by the easy formation of an intermediate a-cyclopropylcarbinyl carbocation. Further reactions lead to products in which the C2–C3 bond of the cyclopropane ring is broken to give compounds with a guaiane skeleton. Guaiane-type dienes and unsaturated cyclic ethers are the final products of these rearrangements. Several derivatives of these compounds have been prepared.
Original languageEnglish
Pages (from-to)7743-7750
Issue number39
Publication statusPublished - 2003


  • oil
  • constituents


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