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Volumn 1, Issue 5, 2010, Pages 609-614

A tangled web-interconnecting pathways to amorphadiene and the amorphene sesquiterpenes

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; FARNESYL DIPHOSPHATE; LOW ENERGIES; NATURAL PRODUCTS; QUANTUM CHEMICAL STUDIES; SESQUITERPENES;

EID: 79952591147     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c0sc00333f     Document Type: Article
Times cited : (28)

References (70)
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    • This is Part 7 in our series of reports on "Theoretical Studies on Farnesyl Cation Cyclization." For parts 1-6, see ref. 7a, 7c, 7e, 7h, 8 and 9. For reviews with leading references to theoretical work by us and others on closely related systems, see
    • F. Lopez-Gallego S. A. Agger D. Abate-Pella M. D. Distefano C. Schmidt-Dannert ChemBioChem 2010 11 1093 1106
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    • Lopez-Gallego, F.1    Agger, S.A.2    Abate-Pella, D.3    Distefano, M.D.4    Schmidt-Dannert, C.5
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    • Et al
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    • Frisch, M.J.1
  • 56
    • 18844424379 scopus 로고    scopus 로고
    • Johannes Kepler University, Linz, A vast array of sesquiterpenes can be derived from the bisabolyl cation. For our previous theoretical work on pathways to some of these, see ref. 7h, 8 and 9 Cation may also be the immediate precursor to β- and γ-curcumene
    • N. Müller, A. Falk and G. Gsaller, Ball & Stick v. 4.0a12, Molecular Graphics Application for MacOS Computers, Johannes Kepler University, Linz, 2004
    • (2004) Ball & Stick V. 4.0a12, Molecular Graphics Application for MacOS Computers , vol.500
    • Müller, N.1    Falk, A.2    Gsaller, G.3
  • 59
    • 2442445180 scopus 로고    scopus 로고
    • and, via further rearrangements, to a variety of other sesquiterpenes 9 Cation B may also be the immediate precursor to β-sesquiphellandrene, zingeberene and γ-curcumene. 23a-c β-Sesquiphellandrene and zingeberene have been detected amongst the mixture of products from the amorphadiene synthase cloned from Artemissia annua L 2,3
    • T. G. Köllner C. Schnee J. Gershenzon J. Degenhardt Plant Cell 2004 16 1115 1131
    • (2004) Plant Cell , vol.16 , pp. 1115-1131
    • Köllner, T.G.1    Schnee, C.2    Gershenzon, J.3    Degenhardt, J.4
  • 61
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    • Similar pathways involving different conformers of cations A, B and C were also examined. See ESI for details
    • G. S. Hammond J. Am. Chem. Soc. 1955 77 334 338
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    • Hammond, G.S.1
  • 63
    • 0008034716 scopus 로고
    • Deprotonation of C2 to form amorphadiene was modeled using ammonia. See ESI for details For leading references, see
    • R. Hoffmann Acc. Chem. Res. 1971 4 1 9
    • (1971) Acc. Chem. Res. , vol.4 , pp. 1-9
    • Hoffmann, R.1
  • 68
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    • Similar pathways involving other conformers (including isopropyl group rotamers) were also examined. See ESI for details For leading references, see
    • W. C. Still I. Galynker Tetrahedron 1981 37 3981 3996
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    • Deprotonation of cations H1 and H2 using an ammonia model was also examined. Complexation of these cations via C-H⋯X interactions involving certain hydrogens did prompt their geometries to become more localized. See ESI for details. Related geometric changes upon complexation have been described previously 7a,f,i,9,18,19
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.