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Volumn 65, Issue 33, 2009, Pages 6535-6548

Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes: construction of the pentacyclic core structure of daphnilactone B

Author keywords

Alkaloid; Nitroalkene; Tandem cycloaddition

Indexed keywords

ACETAL DERIVATIVE; ALKALOID; ALKENE; DAPHNILACTONE B; METHYL GROUP; NITROALKENE; NITROSO DERIVATIVE; NITROSOACETAL; UNCLASSIFIED DRUG;

EID: 67650299282     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.060     Document Type: Article
Times cited : (63)

References (71)
  • 19
    • 67650302163 scopus 로고    scopus 로고
    • Harrington, R. M.; Magnus, P. D. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006.
    • Harrington, R. M.; Magnus, P. D. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006.
  • 22
    • 67650283802 scopus 로고    scopus 로고
    • Fused mode
    • Fused mode:
  • 28
    • 0000394927 scopus 로고
    • Although the nitroalkene cycloaddition is an inverse electron demand process, the electron-withdrawing substituents on the nitroalkene can also effect the Lewis basicity of the nitro group and reduce the equilibrium concentration of the activated complex, see:
    • Although the nitroalkene cycloaddition is an inverse electron demand process, the electron-withdrawing substituents on the nitroalkene can also effect the Lewis basicity of the nitro group and reduce the equilibrium concentration of the activated complex, see:. Denmark S.E., Kesler B.S., and Moon Y.-C. J. Org. Chem. 57 (1992) 4912-4924
    • (1992) J. Org. Chem. , vol.57 , pp. 4912-4924
    • Denmark, S.E.1    Kesler, B.S.2    Moon, Y.-C.3
  • 31
    • 67650302161 scopus 로고    scopus 로고
    • For a full account of the development of a first generation model see
    • For a full account of the development of a first generation model see:
  • 43
    • 67650302162 scopus 로고    scopus 로고
    • note
    • The crystallographic coordinates of 28a and 28b have been deposited with the Cambridge Crystallographic Data Centre, deposition nos. CCDC 282324 and 282325, respectively. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; email: deposit@ccdc.cam.ac.uk).
  • 44
    • 67650323987 scopus 로고    scopus 로고
    • note
    • 13C NMR, COSY, HMBC, HMQC, and mass spectrometric analysis, see the Supplementary data for details.
  • 45
    • 28844466070 scopus 로고    scopus 로고
    • For a review of tandem oxidation/olefination sequences see:
    • For a review of tandem oxidation/olefination sequences see:. Taylor R.J.K., Reid M., Foot J., and Raw S.A. Acc. Chem. Res. 38 (2008) 851-869
    • (2008) Acc. Chem. Res. , vol.38 , pp. 851-869
    • Taylor, R.J.K.1    Reid, M.2    Foot, J.3    Raw, S.A.4
  • 46
    • 67650323986 scopus 로고    scopus 로고
    • note
    • Trityllithium was used to avoid a conjugate acid that retained any Brønsted basicity such as a secondary amine.
  • 47
    • 67650326924 scopus 로고    scopus 로고
    • note
    • Interestingly, even when 1.0 equiv of base and 1.0 equiv of TBSCl were used, a 50:50 mixture of starting material and bis-silylated product was obtained.
  • 48
    • 67650305504 scopus 로고    scopus 로고
    • note
    • Reaction with 1.0 equiv of iodine provided a complex reaction mixture.
  • 49
    • 67650305506 scopus 로고    scopus 로고
    • note
    • Preliminary studies on the cycloaddition of 18 and further elaboration of the cycloadducts were carried out on racemic material through compounds 68a/68b. However, unless otherwise specified, the results described herein are for enantiomerically enriched materials.
  • 51
    • 67650286928 scopus 로고    scopus 로고
    • note
    • The crystallographic coordinates of 58a and 58b have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 675071. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; via the website www.ccdc.cam.ac.uk/conts/retrieving.html or deposit@ccdc.cam.ac.uk.
  • 53
    • 67650323985 scopus 로고    scopus 로고
    • note
    • The crystallographic coordinates of 67b have been deposited with the Cambridge Crystallographic Data Centre, deposition no. CCDC 632323. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax +44 1223 336 033; email: deposit@ccdc.cam.ac.uk).
  • 54
    • 67650283800 scopus 로고    scopus 로고
    • note
    • +-Bu), which is similar to the MS analysis of 67a (452.2, 2.9%; 410.2, 100%).
  • 67
    • 67650333174 scopus 로고    scopus 로고
    • note
    • Raney nickel from Grace Davidson, grade 6800 was used for these hydrogenations.
  • 69
    • 67650308561 scopus 로고    scopus 로고
    • note
    • 3: 175.9, 174.3, 167.6, 86.8, 77.8, 76.1, 65.3, 62.0. IR (NaCl): 1734, 1764.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.