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Volumn 51, Issue 3, 2010, Pages 503-507

From aromatics to conjoined inositols: stereoselective oxyfunctionalization of anthracene

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE; AROMATIC COMPOUND; INOSITOL DERIVATIVE;

EID: 71749107589     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.054     Document Type: Article
Times cited : (15)

References (77)
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    • For reviews dealing with chemistry and the biology of inositols, see:
    • For reviews dealing with chemistry and the biology of inositols, see:. Berridge M.J., and Irvine R.F. Nature 312 (1984) 315-321
    • (1984) Nature , vol.312 , pp. 315-321
    • Berridge, M.J.1    Irvine, R.F.2
  • 7
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    • Taylor C.W. Cell 111 (2002) 767-769
    • (2002) Cell , vol.111 , pp. 767-769
    • Taylor, C.W.1
  • 15
    • 34248548513 scopus 로고    scopus 로고
    • Irvine R. Science 316 (2007) 845-846
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    • Irvine, R.1
  • 45
    • 0034700565 scopus 로고    scopus 로고
    • We have been concurrently interested in the synthesis of polycyclic polyoxygenated molecular scaffolds which are based on fused cyclohexane rings and are known for their wide-ranging biological activity, see:
    • We have been concurrently interested in the synthesis of polycyclic polyoxygenated molecular scaffolds which are based on fused cyclohexane rings and are known for their wide-ranging biological activity, see:. Mehta G., and Ramesh S.S. Chem. Commun. (2000) 2429-2430
    • (2000) Chem. Commun. , pp. 2429-2430
    • Mehta, G.1    Ramesh, S.S.2
  • 67
    • 0037019971 scopus 로고    scopus 로고
    • While the stereoselectivity noted during the bromination of 15 may be regarded as an extension of the well-known Fürst-Plattner rule for epoxide ring opening (see Ref. 14), an explanation for the regioselectivity observed in the same reaction is far less obvious. Putatively, the regioselectivity observed here may be attributed to a greater through-space electronic stabilization of the incipient bromonium ion by one or other of the two homoallylic hydroxy groups present in 15. See:
    • While the stereoselectivity noted during the bromination of 15 may be regarded as an extension of the well-known Fürst-Plattner rule for epoxide ring opening (see Ref. 14), an explanation for the regioselectivity observed in the same reaction is far less obvious. Putatively, the regioselectivity observed here may be attributed to a greater through-space electronic stabilization of the incipient bromonium ion by one or other of the two homoallylic hydroxy groups present in 15. See:. Chiappe C., De Rubertis A., Jaber A., Lenoir D., Wattenbach C., and Pomelli C.S. J. Org. Chem. 67 (2002) 7066-7074
    • (2002) J. Org. Chem. , vol.67 , pp. 7066-7074
    • Chiappe, C.1    De Rubertis, A.2    Jaber, A.3    Lenoir, D.4    Wattenbach, C.5    Pomelli, C.S.6
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    • Fürst, A.; Plattner, P. A. Abstr. Papers Int. Congr. Pure Appl. Chem., 12th, New York, 1951, 40.
    • Fürst, A.; Plattner, P. A. Abstr. Papers Int. Congr. Pure Appl. Chem., 12th, New York, 1951, 40.
  • 72
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    • note
    • +: 419.0317; found: 419.0353; 32 mp 220 °C (chars before melting); IR
  • 73
    • 71749110866 scopus 로고    scopus 로고
    • note
    • 2 = 0.0758 for 3045 observed reflections, CCDC 752351.
  • 74
    • 71749090540 scopus 로고    scopus 로고
    • note
    • The mechanism for the acid-catalyzed rearrangement ('acetate dance') is shown below:{A figure is presented}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.