Tetrahedron

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

FJ Moreno-Dorado, YMAW Lamers, G Mironov…

Index: Moreno-Dorado, F. Javier; Lamers, Yvonne M. A. W.; Mironov, Grigore; Wijnberg, Joannes B. P. A.; De Groot, Aede Tetrahedron, 2003 , vol. 59, # 39 p. 7743 - 7750

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Citation Number: 13

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 β-side. Under acidic conditions its C7–C8 β-epoxide and β-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 ...