## Bergamotene ( 2) has been synthesized in five steps from geranylacetone using intramolecular ketene-olefin cycloaddition as a key step. We have recently completed a synthesis of retigeranic acid (L )l in which the pentacyclic system was generated by intramolecular cycloaddition of the ketene2
Structure of β-bergamotene
✍ Scribed by K.S. Kulkarni; S.K. Paknikar; A.S. Vaidya; G.R. Kelkar; R.B. Bates; S.C. Bhattacharyya
- Publisher
- Elsevier Science
- Year
- 1963
- Tongue
- French
- Weight
- 287 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The recent commlmication by Buchi &&. 1 on the structure of calarene prompts us to record some of the results of our investigation on the constituents of solvent extracted oil of Valerisna Wallichi (Fam. Valerianaceae), a species of Indian origin. From the hydrocarbon fraction, we have been able to isolate two pure2 sesquiterpene hydrocarbons by extensive chromatography over alumina. The first of these, Hydrocarbon A, C1#?*3 in its NMR spectrum' exhibited signals at 4.78(;C = C /H \C-H) *. 1. 506 Structure of P-bergamotene No.8 g.g3, 8.95, 9.01 (three methyl-groups not bonded to any double bond); 9.16 and 9.39 .y (CyClOpropyl prOtOnS).
Though the infrared spectra of this hydrocarbon and its dihydro derivative showed great similarity with that of calarene and calarane respectively, we were not able to prove its identity with calarene, since the ccnotants reported by Sorm e&&5 were considerably different from those recorded on our sample.
while we were engaged on the structural studies of these compounds, Buchi and coworkers 1 proposed structure (1) for calarene. The physical constants and NMR data recorded by these authors Proved the iientity of 'Hydrocarbon 41 with
Calarene. @UT reS9ltS
📜 SIMILAR VOLUMES
Recently Bhattacharyya et al. --(1) isolated a new sesquiterpene hydrocarbon from Indian valerian root oil, which was named S-bergamotene, and assigned structure 1. On the basis of a comparison of the chemical shift of the quaternary methyl group in g-bergamotene with the chemical shifts of the met
Swnmary: Feeding of [12, 13-13C]-~trans-bergamotene to cultures of Pseudeurotium ovalis resulted in labeling of C-12 and C-13 of the antibiotic ovalicin, as established by 13C NMR.
Recent work in this laboratory' and elsewhere3 has implicated the sesquiterpene hydrocarbon B-trans-bergamotene (2) in the biosynthesis of the immunosuppressive antibiotic ovalicin 4 (2). Incorporation experiments using both