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Volumn 66, Issue 51, 2010, Pages 9667-9674

The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

Author keywords

Heterocycle; Macrocycle; Mechanism; Oxidative fragmentation; VT NMR analysis

Indexed keywords

10 (3 CHLOROPHENYL) 6,8,9,10 TETRAHYDROBENZO[B][1,8]NAPHTHYRIDIN 5(7H)ONE; 12 (3 CHLOROPHENYL) 7,8,9,10 TETRAHYDROPYRIDO[2,3 B]AZECINE 5,6,11(12H)TRIONE; ANTIPSORIASIS AGENT; RUTHENIUM DERIVATIVE; RUTHENIUM TETROXIDE; UNCLASSIFIED DRUG; WATER;

EID: 78650191635     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.044     Document Type: Article
Times cited : (7)

References (31)
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    • For recent reviews see
    • For recent reviews see:
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    • For detailed discussion of atropisomerism see
    • For detailed discussion of atropisomerism see:
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    • 3
    • 3
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    • 3 was observed
    • 3 was observed.
  • 17
    • 78650227754 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for 2 and syn-11 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 741362 and 741363. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44(0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk)
    • Crystallographic data (excluding structure factors) for 2 and syn-11 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 741362 and 741363. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44(0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ).
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    • For a more detailed discussion see Supplementary data
    • For a more detailed discussion see Supplementary data.
  • 19
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    • Lead tetraacetate is known to undergo both a concerted fragmentation that is rapid with syn-diols and also a much slower reaction to cleave anti-diols. The speed of the reaction reported here was consistent with the structure of syn-diol 11. For a recent example of the use of lead tetraacetate to cleave a syn-diol in the context of natural product synthesis see E.F. Makiyi, R.F.M. Frade, T. Lebl, E.G. Jaffray, S.E. Cobb, A.L. Harvey, A.M.Z. Slawin, R.T. Hay, and N.J. Westwood Eur. J. Org. Chem. 33 2009 5711 5715
    • (2009) Eur. J. Org. Chem. , vol.33 , pp. 5711-5715
    • Makiyi, E.F.1    Frade, R.F.M.2    Lebl, T.3    Jaffray, E.G.4    Cobb, S.E.5    Harvey, A.L.6    Slawin, A.M.Z.7    Hay, R.T.8    Westwood, N.J.9
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    • We thank the reviewers for raising these issues during the assessment of this manuscript. We would also like to thank the authors of Ref. 3 for help and advice throughout the review process
    • We thank the reviewers for raising these issues during the assessment of this manuscript. We would also like to thank the authors of Ref. 3 for help and advice throughout the review process.
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    • 4 see B. Plietker - Synthesis 15 2005 2453 2472
    • (2005) Synthesis , vol.15 , pp. 2453-2472
    • Plietker, B.1
  • 27
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    • For a recent review of the use of ruthenium-based catalysed in epoxidation reactions see D. Chatterjee Coord. Chem. Rev. 252 2008 176 198
    • (2008) Coord. Chem. Rev. , vol.252 , pp. 176-198
    • Chatterjee, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.