74409-93-1Relevant articles and documents
Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides
Moreno-Dorado, F. Javier,Lamers, Yvonne M. A. W.,Mironov, Grigore,Wijnberg, Joannes B. P. A.,De Groot, Aede
, p. 7743 - 7750 (2003)
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 isoledene and its α-epoxide, under acidic conditions, is governed by the easy formation of an intermediate α-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.
NEW TERPENOIDS OF THE ESSENTIAL OIL OF LEDUM PALUSTRE
Belousova, N. I.,Tkachev, A. V.,Shakirov, M. M.,Khan, V. A.
, p. 20 - 24 (2007/10/02)
The structures of two new natural compounds isolated from the essential oil of Ledum palustre L. have been established on the basis of their spectral characteristics as p-mentha-1,8(10)-diene 3,9-epoxide (lepaloks) and 3,10-epoxygermacr-4(14)-en-8-one (lepakson).The chemical structure of ledene as a sesquiterpene hydrocarbon has been determined by chemical correlation.
Katalytische Umwandlung von Sesquiterpenkohlenwasserstoffen an Alkalimetall/Aluminiumoxid-Kontakten
Rienaecker, Roland,Graefe, Juergen
, p. 348 - 349 (2007/10/02)
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