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Volumn , Issue 8, 1999, Pages 731-732

The cyclization mechanism of squalene in hopene biosynthesis: The terminal methyl groups are critical to the correct folding of this substrate both for the formation of the five-membered E-ring and for the initiation of the polycyclization reaction

Author keywords

[No Author keywords available]

Indexed keywords

METHYL GROUP; SQUALENE;

EID: 0033591019     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901351b     Document Type: Article
Times cited : (30)

References (14)
  • 6
    • 0029962996 scopus 로고    scopus 로고
    • E. J. Corey, S. C. Virgil, H. Cheng, C. H. Baker, S. P. T. Matsuda, V. Singh and S. Sarshar, J. Am. Chem. Soc., 1995, 117, 11 819; E. J. Corey and H. Cheng, Tetrahedron Lett., 1996, 37, 2709; T. Hoshino and Y. Sakai, Chem. Commun., 1998, 1591.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2709
    • Corey, E.J.1    Cheng, H.2
  • 7
    • 21844478741 scopus 로고    scopus 로고
    • E. J. Corey, S. C. Virgil, H. Cheng, C. H. Baker, S. P. T. Matsuda, V. Singh and S. Sarshar, J. Am. Chem. Soc., 1995, 117, 11 819; E. J. Corey and H. Cheng, Tetrahedron Lett., 1996, 37, 2709; T. Hoshino and Y. Sakai, Chem. Commun., 1998, 1591.
    • (1998) Chem. Commun. , pp. 1591
    • Hoshino, T.1    Sakai, Y.2
  • 9
    • 0344143681 scopus 로고    scopus 로고
    • note
    • 1H COSY 45, HOHAHA, NOESY, DEPT, HMQC and HMBC) unequivocally supported the structures of 5, 6, 7, 8 and 12.
  • 13
    • 0344143680 scopus 로고    scopus 로고
    • note
    • Given that a water molecule attacks in the axial direction, a more hindered interaction would occur between the LUMO at C17-C18 and the HOMO at C21-C22 due to constrained overlapping (carbon numbering shown in Scheme 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.