- EREMOPHILENE AND GERMACRENE DERIVATIVES FROM SENECIO GLANDULOSO-PILOSUS
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Senecio glanduloso-pilosus afforded in addition to known compounds a new eremophilene derivative and a hydroperoxide from germacrene D. - Key Word Index: Senecio glanduloso-pilosus; Compositae; sesquiterpenes; eremophilene derivative; germacrene hydroperoxide.
- Bohlmann, Ferdinand,Gupta, Rajinder K.
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- Enantiomeric Resolution of a Germacrene-D Derivative by Chiral High-performance Liquid Chromatography
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Direct enantiomeric resolution of the germacrene-D derivative, (5E,7S*,9S*)-9-hydroxy-7-isopropyl-4,10-bis(methylene)-5-cyclodecen- 1-one, was carried out by HPLC with a chiral stationary phase. This method showed that germacrene-D contained in ylang ylang oil was 98% e.e., whereas germacrene-D extracted from Solidago altissima L. was almost racemic.
- Nishii, Yoshinori,Yoshida, Taichi,Tanabe, Yoo
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- Total synthesis of (-)-periplanones C and D. Their pheromonal activities against three Periplaneta species
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Total synthesis of(-)-periplanones C [(-)-PC; 1] and D [(-)-PD; 2] was achieved starting from (-)-germacrene D via 7 and 8 steps, respectively, according to the similar route on syntheses of racemic PC and PD. The 1H NMR and GC mass spectra of 2 unambiguously determined the structure of the natural sample of PD which was isolated from Periplaneta fuliginosa. Bioassay of synthetic samples of 1 and 2 was carried oat against males of P. fuliginosa, P. americana, and P. japonica. 10-9 g of 1 elicited significant response in males of P. americana and P. japonica. 10-10 g of 2 elicited strong response in P. fuliginosa males, whereas it showed significantly weak response against males of P. americana and P. japonica. Almost same degree of activities was observed between 1 and 2 against males of P. americana and P. japonica at 10-10 g dose.
- Nishii, Yoshinori,Watanabe, Keisuke,Yoshida, Taichi,Okayama, Tatsutoshi,Takahashi, Shozo,Tanabe, Yoo
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p. 7209 - 7218
(2007/10/03)
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- THE SYNTHESIS OF A TRICYCLIC HYDROAZULENONE FROM EXO-EPOXYGERMACRENE-D IN CONNECTION WITH PERIPLANONE A
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In connection with periplanone A, acid-catalyzed reaction of germacrene-D epoxide has been carried out using AlCl3 in ether to afford a hydroazulene which has been further transformed into one of the hydroazulenones proposed to be periplanone A.
- Shizuri, Yoshikazu,Yamaguchi, Shu,Yamamura, Shosuke,Ishihara, Makoto,Ohba, Shigeru,et al.
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p. 3831 - 3834
(2007/10/02)
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- Constituents of Torilis japonica D.C. I. Isolation and Optical Purity of Germacra-4(15),5(E),10(14)-trien-1β-ol
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Humulene (I), (-)-germacrene-D (II), and (-)-germacra-4(15),5(E),10(14)-trien-1β-ol (III) were isolated from the fruits of Torilis japonica.The latter two compounds (II and III) were determined to have optical purities of about 40 and 30percent, respectively.Keywords-Torilis japonica; humulene; germacrene-D; germacra-4(15),5(E),10(14)-trien-1β-ol; optical purity
- Itokawa, Hideji,Matsumoto, Hajime,Mihashi, Susumu
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p. 1743 - 1745
(2007/10/02)
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