메뉴 건너뛰기




Volumn 52, Issue 42, 2013, Pages 11029-11033

The concerted nature of the cyclization of squalene oxide to the protosterol cation

Author keywords

carbocations; density functional calculations; reaction mechanisms; squalene; terpenoids

Indexed keywords

BOAT CONFORMATIONS; CARBOCATIONS; REACTION MECHANISM; RING FORMATION; SQUALENE; TERPENOIDS;

EID: 84885442213     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302886     Document Type: Article
Times cited : (26)

References (43)
  • 6
    • 0000558630 scopus 로고
    • D. U. Cane, Chem. Rev. 1990, 90, 1089-1103
    • (1990) Chem. Rev. , vol.90 , pp. 1089-1103
    • Cane, D.U.1
  • 8
  • 29
    • 77952083065 scopus 로고    scopus 로고
    • Geometries were optimized without symmetry constraints using BB1K/6-31G
    • Geometries were optimized without symmetry constraints using BB1K/6-31G* (, M. Weitman, D. T. Major, J. Am. Chem. Soc. 2010, 132, 6349-6360
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6349-6360
    • Weitman, M.1    Major, D.T.2
  • 32
    • 33748545144 scopus 로고
    • All structures were characterized by frequency calculations, and reported energies include zero-point energy corrections (unscaled). Intrinsic reaction coordinate (IRC) calculations
    • P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222). All structures were characterized by frequency calculations, and reported energies include zero-point energy corrections (unscaled). Intrinsic reaction coordinate (IRC) calculations
    • (1973) Theor. Chim. Acta , vol.28 , pp. 213-222
    • Hariharan, P.C.1    Pople, J.A.2
  • 34
    • 33751044609 scopus 로고
    • were also used to verify the identity of all transition structures
    • K. Fukui, Acc. Chem. Res. 1981, 14, 363-368) were also used to verify the identity of all transition structures.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 363-368
    • Fukui, K.1
  • 36
    • 33645216534 scopus 로고    scopus 로고
    • Our earlier calculation on this C-ring expansion/D-ring formation was carried out with B3LYP/6-31G*, which both Matsudaand Major
    • Our earlier calculation on this C-ring expansion/D-ring formation was carried out with B3LYP/6-31G*, which both Matsuda (, S. P. T. Matsuda, W. K. Wilson, Q. Xiong, Org. Biomol. Chem. 2006, 4, 530-543) and Major
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 530-543
    • Matsuda, S.P.T.1    Wilson, W.K.2    Xiong, Q.3
  • 37
    • 77952083065 scopus 로고    scopus 로고
    • have noted does not give reliable energies for cyclizations of hydrocarbons. Major has found that the BB1K method on the other hand does
    • M. Weitman, D. T. Major, J. Am. Chem. Soc. 2010, 132, 6349-6360) have noted does not give reliable energies for cyclizations of hydrocarbons. Major has found that the BB1K method on the other hand does.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6349-6360
    • Weitman, M.1    Major, D.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.