메뉴 건너뛰기




Volumn 77, Issue 2, 2012, Pages 825-842

An approach to mimicking the sesquiterpene cyclase phase by nickel-promoted diene/alkyne cooligomerization

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; COOLIGOMERIZATION; CYCLASES; MATERIALS INDUSTRY; MOLECULAR COMPLEXITY; NICKEL CATALYSIS; SESQUITERPENES; SYNTHETIC STRATEGIES; TERPENE BIOSYNTHESIS; ZEROVALENT;

EID: 84856084692     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202314a     Document Type: Article
Times cited : (17)

References (86)
  • 6
    • 0033582442 scopus 로고    scopus 로고
    • For a review that focuses on the syntheses of germacrane sesquiterpenes, see.
    • For a review that focuses on the syntheses of germacrane sesquiterpenes, see: Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1999, 55, 2115-2146.
    • (1999) Tetrahedron , vol.55 , pp. 2115-2146
    • Minnaard, A.J.1    Wijnberg, J.B.P.A.2    De Groot, A.3
  • 11
    • 0002254531 scopus 로고
    • Conversion of acetyl coenzyme A to isopentenyl pyrophosphate
    • In; John Wiley & Sons: New York, Vol.
    • Spurgeon, S. L.; Porter, J. W. Conversion of acetyl coenzyme A to isopentenyl pyrophosphate. In Biosynthesis of Isoprenoid Compounds; John Wiley & Sons: New York, 1981; Vol. 1, pp 1-93.
    • (1981) Biosynthesis of Isoprenoid Compounds , vol.1 , pp. 1-93
    • Spurgeon, S.L.1    Porter, J.W.2
  • 13
    • 0037062894 scopus 로고    scopus 로고
    • references cited therein
    • Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441-2443 and references cited therein
    • (2002) J. Org. Lett. , vol.4 , pp. 2441-2443
    • Hu, T.1    Corey, E.2
  • 23
    • 84856117654 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Buchkremer, J. Ph.D. Thesis, University of Bochum, 1973.
    • (1973)
    • Buchkremer, J.1
  • 25
    • 84856117656 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Kopp, W. Ph.D. Thesis, University of Bochum, 1970.
    • (1970)
    • Kopp, W.1
  • 27
    • 84856117657 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Selbeck, H. Ph.D. Thesis, University of Bochum, 1972.
    • (1972)
    • Selbeck, H.1
  • 36
    • 84856086912 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Hey, H.-J. Ph.D. Thesis, University of Bochum, 1969.
    • (1969)
    • Hey, H.-J.1
  • 37
    • 84856117658 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Wiese, W. Ph.D. Thesis, University of Bochum, 1969.
    • (1969)
    • Wiese, W.1
  • 40
    • 84856120031 scopus 로고
    • 0-catalyzed construction of 5-membered rings from 1,5-cyclooctadiene, see: Ph.D. Thesis, University of Bochum.
    • 0-catalyzed construction of 5-membered rings from 1,5-cyclooctadiene, see: Nüssel, H.-G. Ph.D. Thesis, University of Bochum, 1970.
    • (1970)
    • Nüssel, H.-G.1
  • 47
    • 84856117663 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Meyer, R.-V. Ph.D. Thesis, University of Bochum, 1973.
    • (1973)
    • Meyer, R.-V.1
  • 48
    • 84856086918 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Buchholz, H. A. Ph.D. Thesis, University of Bochum, 1971.
    • (1971)
    • Buchholz, H.A.1
  • 49
    • 84856086917 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Büssemeier, B. Ph.D. Thesis, University of Bochum, 1973.
    • (1973)
    • Büssemeier, B.1
  • 50
    • 84856120032 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Thömel, F. Ph.D. Thesis, University of Bochum, 1970.
    • (1970)
    • Thömel, F.1
  • 57
  • 58
    • 84981905416 scopus 로고
    • A similar, although mechanistically distinct, phenomenon regarding the oligomerization of ethylene is called the "nickel effect:"
    • A similar, although mechanistically distinct, phenomenon regarding the oligomerization of ethylene is called the "nickel effect:" Fischer, K.; Jonas, K.; Misbach, P.; Stabba, R.; Wilke, G. Angew. Chem., Int. Ed. 1973, 12, 943-953
    • (1973) Angew. Chem., Int. Ed. , vol.12 , pp. 943-953
    • Fischer, K.1    Jonas, K.2    Misbach, P.3    Stabba, R.4    Wilke, G.5
  • 59
    • 0003415078 scopus 로고    scopus 로고
    • Group 10 (Ni, Pd, Pt) Metal Compounds
    • In; Komiya, S. John Wiley & Sons Ltd. New York
    • Ozawa, F. Group 10 (Ni, Pd, Pt) Metal Compounds. In Synthesis of Organometallic Compounds; Komiya, S., Ed.; John Wiley & Sons Ltd.: New York, 1997; pp 249-303.
    • (1997) Synthesis of Organometallic Compounds , pp. 249-303
    • Ozawa, F.1
  • 60
    • 84856117660 scopus 로고
    • 2 with organoaluminum reagents, see: Ph.D. Thesis, University of Bochum.
    • 2 with organoaluminum reagents, see: Misbach, P. Ph.D. Thesis, University of Bochum, 1969.
    • (1969)
    • Misbach, P.1
  • 61
    • 84856117662 scopus 로고
    • For detailed investigations on the complexity of conformational isomerism in π -allyl nickel systems, see: Ph.D. Thesis, University of Bochum.
    • For detailed investigations on the complexity of conformational isomerism in π -allyl nickel systems, see: Schenkluhn, H. Ph.D. Thesis, University of Bochum, 1971.
    • (1971)
    • Schenkluhn, H.1
  • 65
    • 0037032221 scopus 로고    scopus 로고
    • For theoretical work on hapticity in butadiene dimerization, see
    • For theoretical work on hapticity in butadiene dimerization, see: Tobisch, S.; Ziegler, T. J. Am. Chem. Soc. 2002, 124, 13290-13301
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13290-13301
    • Tobisch, S.1    Ziegler, T.2
  • 66
    • 58249126738 scopus 로고    scopus 로고
    • There are examples of (4 E,10 Z), (4 Z,10 E), (4 Z,10 Z) germacrene natural products; however, they are in the minority. For several examples, see
    • There are examples of (4 E,10 Z), (4 Z,10 E), (4 Z,10 Z) germacrene natural products; however, they are in the minority. For several examples, see: Adio, A. M. Tetrahedron 2009, 65, 1533-1552
    • (2009) Tetrahedron , vol.65 , pp. 1533-1552
    • Adio, A.M.1
  • 67
    • 84981880002 scopus 로고
    • A different metal may also change the outcome, for example it is known that titanium catalysts produce primarily 1,5,9- cis, trans, trans -cyclododecatriene, whereas nickel and chromium afford the respective all-trans isomer
    • A different metal may also change the outcome, for example it is known that titanium catalysts produce primarily 1,5,9- cis, trans, trans -cyclododecatriene, whereas nickel and chromium afford the respective all-trans isomer: Weber, H.; Ring, W.; Hochmuth, U.; Franke, W. Liebigs Ann. Chem. 1965, 681, 10-20
    • (1965) Liebigs Ann. Chem. , vol.681 , pp. 10-20
    • Weber, H.1    Ring, W.2    Hochmuth, U.3    Franke, W.4
  • 70
    • 84856117661 scopus 로고
    • Ph.D. Thesis, University of Bochum.
    • Fleck, W. Ph.D. Thesis, University of Bochum, 1971.
    • (1971)
    • Fleck, W.1
  • 73
    • 0013559027 scopus 로고
    • For implications in synthesis, see, for example
    • For implications in synthesis, see, for example: Kodama, M.; Yokoo, S.; Matsuki, Y.; Ito, S. Tetrahedron Lett. 1979, 20, 1687-1690
    • (1979) Tetrahedron Lett. , vol.20 , pp. 1687-1690
    • Kodama, M.1    Yokoo, S.2    Matsuki, Y.3    Ito, S.4
  • 77
    • 33847804260 scopus 로고
    • Electron-poor alkynes have been incorporated into 10-membered rings in a related stoichiometric experiment at low temperature
    • Electron-poor alkynes have been incorporated into 10-membered rings in a related stoichiometric experiment at low temperature: Büssemeier, B.; Jolly, P. W.; Wilke, G. J. Am. Chem. Soc. 1974, 94, 4726-4727
    • (1974) J. Am. Chem. Soc. , vol.94 , pp. 4726-4727
    • Büssemeier, B.1    Jolly, P.W.2    Wilke, G.3
  • 85
    • 0037463419 scopus 로고    scopus 로고
    • For benzonitrile cross-couplings, see
    • For benzonitrile cross-couplings, see: Miller, J. A.; Dankwardt, J. W. Tetrahedron Lett. 2002, 44, 1907-1910
    • (2002) Tetrahedron Lett. , vol.44 , pp. 1907-1910
    • Miller, J.A.1    Dankwardt, J.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.