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Volumn , Issue 11, 2010, Pages 2182-2198

Preparation of 9α-fluorinated sesquiterpenic drimanes and evaluation of their antifeedant activities

Author keywords

Biological activity; Fluorine; Natural products; Terpenoids; Total synthesis

Indexed keywords


EID: 77950208252     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901499     Document Type: Article
Times cited : (24)

References (148)
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    • Jaeckel, C.1    Koksch, B.2
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    • For simplicity, the usual drimane nomenclature and numbering is used for all bicyclic compounds
    • For simplicity, the usual drimane nomenclature and numbering is used for all bicyclic compounds.
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    • According to the LUMO energy calculations, the LUMO energy of the π-CO bond is lowered by ca. 6.5 kcal/mol by the effect of the fluorine atom. LUMO energies were determined after optimizing the molecular geometry for 11 and 19, first, by using the MM3 force-field and then by using MOPAC with the standard PM3 parameter set (CAChe WorkSystem Pro Version 7.5.0.85, Fujitsu Ltd., Tokyo, Japan). Most probably, the long reaction time required for the complete conversion of 19 to 22 see the Supporting Information must also be due to the acid-basic equilibrium that exists between, the β-keto ester moiety and the phosphorus ylide
    • According to the LUMO energy calculations, the LUMO energy of the π-CO bond is lowered by ca. 6.5 kcal/mol by the effect of the fluorine atom. LUMO energies were determined after optimizing the molecular geometry for 11 and 19, first, by using the MM3 force-field and then by using MOPAC with the standard PM3 parameter set (CAChe WorkSystem Pro Version 7.5.0.85, Fujitsu Ltd., Tokyo, Japan). Most probably, the long reaction time required for the complete conversion of 19 to 22 (see the Supporting Information) must also be due to the acid-basic equilibrium that exists between, the β-keto ester moiety and the phosphorus ylide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.