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

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17 Citations (Scopus)

Abstract

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
JournalTetrahedron
Volume59
Issue number39
DOIs
Publication statusPublished - 2003

Keywords

  • oil
  • constituents

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    Moreno-Dorado, F. J., Lamers, Y. M. A. W., Mironov, G., Wijnberg, J. B. P. A., & de Groot, Æ. (2003). Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides. Tetrahedron, 59(39), 7743-7750. https://doi.org/10.1016/S0040-4020(03)01231-6