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Volumn 21, Issue 17, 2010, Pages 2108-2116

Asymmetric dihydroxylation of drim-7-en-11-ol: Synthesis of diastereomerically pure driman-7α,8α,11-triol and its elaboration into novel chlorinated norlabdanic compounds

Author keywords

[No Author keywords available]

Indexed keywords

13,14,15,16 TETRANORLABD 12 DICHLORO 7ALPHA ACETOXY 8ALPHA OL 11 ONE; 14,15 BISNORLABD 12 ENE 12 CHLORO 8ALPHA,13 EPOXY 7ALAPHA OL 11 ONE; DITERPENE; DRIM 7 EN 11 OL; DRIMAN 7ALPHA,8ALPHA,11 TRIOL; UNCLASSIFIED DRUG;

EID: 77956185324     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.06.029     Document Type: Article
Times cited : (5)

References (59)
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    • In this article, we use the atom numbering of drimanic sesquiterpenes and labdanic diterpenoids according to: Nomenclature of Organic Compounds. Section D, E, F and H, Pergamon Press: Oxford-New-York-Toronto, 1979
    • In this article, we use the atom numbering of drimanic sesquiterpenes and labdanic diterpenoids according to: Nomenclature of Organic Compounds. Section D, E, F and H, Pergamon Press: Oxford-New-York-Toronto, 1979.
  • 37
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    • Potassium permanganate (Eremenko, L. T.; Korolev, A. M. Izv. AN SSSR Ser. Khim. 1970, 1, 147-149) or iodine-copper(II) acetate (Horiuchi, C. A.; Saton, J. Y. Chem. Lett. 1988, 1209-1210) occurred rather slowly, giving complex mixtures of compounds, along with unreacted initial material. Only cetyltrimethylammonium permanganate (Bhushan, V.; Rathore, R.; Chandrasekaran, S. Synthesis 1984, 431-433) afforded driman-7α,8α,11-triol 6 in 17% yield after silica gel column chromatography
    • Potassium permanganate (Eremenko, L. T.; Korolev, A. M. Izv. AN SSSR Ser. Khim. 1970, 1, 147-149) or iodine-copper(II) acetate (Horiuchi, C. A.; Saton, J. Y. Chem. Lett. 1988, 1209-1210) occurred rather slowly, giving complex mixtures of compounds, along with unreacted initial material. Only cetyltrimethylammonium permanganate (Bhushan, V.; Rathore, R.; Chandrasekaran, S. Synthesis 1984, 431-433) afforded driman-7α,8α,11-triol 6 in 17% yield after silica gel column chromatography.
  • 39
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    • Microencapsulated osmium tetraoxide (5 mol %) in the presence of NMO as co-oxidant did not work in the case of our substrate
    • Microencapsulated osmium tetraoxide (5 mol %) in the presence of NMO as co-oxidant (Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094-6095) did not work in the case of our substrate.
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    • Nagayama, S.1    Endo, M.2    Kobayashi, S.J.3
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    • While running the third cycle of the reaction, a considerable amount of initial compound was detected after 20 h. Therefore, an additional reagent mixture (one third of original) was added and stirring at 50 °C was continued for 5 h. The usual work-up gave compounds 6, 7 and 8 in ca. 4:1:3 ratio, 94% overall yield
    • While running the third cycle of the reaction, a considerable amount of initial compound was detected after 20 h. Therefore, an additional reagent mixture (one third of original) was added and stirring at 50 °C was continued for 5 h. The usual work-up gave compounds 6, 7 and 8 in ca. 4:1:3 ratio, 94% overall yield.
  • 53
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    • 8c)
    • 8c).
  • 56
    • 0043098241 scopus 로고    scopus 로고
    • Transl. from Izv. Akad. Nauk. Ser. Khimicheskaya 1996, 11, 2785-2789
    • Aricu, A. N.; Andreeva, I. I.; Vlad, P. F. Russ. Chem. Bull. 1996, 45, 2644-2648 (Transl. from Izv. Akad. Nauk. Ser. Khimicheskaya 1996, 11, 2785-2789).
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    • Aricu, A.N.1    Andreeva, I.I.2    Vlad, P.F.3
  • 58
    • 77956182289 scopus 로고    scopus 로고
    • We are indebted to Dr. Mehdi Rajabi from the Laboratory of Biochemistry and Molecular Biology, Department of Medicine, Surgery and Dentistry, Faculty of Medicine, Polo Universitario S. Paolo, University of Milan, for his experiments with cancer cell lines
    • We are indebted to Dr. Mehdi Rajabi from the Laboratory of Biochemistry and Molecular Biology, Department of Medicine, Surgery and Dentistry, Faculty of Medicine, Polo Universitario S. Paolo, University of Milan, for his experiments with cancer cell lines.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.