- Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene
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(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D. Let nature be your guide! A concise synthesis of the terpene (+)-bicyclogermacrene enables its use as a platform for a fast access to a range of different terpenoids of the aromadendrene family and meroterpenoids of the psiguadial family (see scheme).
- Tran, Duc N.,Cramer, Nicolai
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p. 10654 - 10660
(2014/11/07)
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- Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides
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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.
- Moreno-Dorado, F. Javier,Lamers, Yvonne M. A. W.,Mironov, Grigore,Wijnberg, Joannes B. P. A.,De Groot, Aede
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p. 7743 - 7750
(2007/10/03)
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- NEW TERPENOIDS OF THE ESSENTIAL OIL OF LEDUM PALUSTRE
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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.
- Belousova, N. I.,Tkachev, A. V.,Shakirov, M. M.,Khan, V. A.
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- THE STRUCTURES OF SESQUITERPENE GLYCOSIDES FROM Pittosporum tobira Ait
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The structures of two new sesquiterpene glycosides, pittosporanoside A1 and A2 isolated from the title plant were determined on the basis of chemical and spectral evidence and X-ray crystal structure analysis.
- Takaoka, Daisuke,Kawahara, Hiroshi,Ochi, Shima,Hiroi, Mitsuru,Nozaki, Hiroshi,et al.
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p. 1121 - 1124
(2007/10/02)
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