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Volumn 67, Issue 1, 2011, Pages 179-192

Tandem Wittig-intramolecular Diels-Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating

Author keywords

1,3,9 Decatriene; 1 Oxo 3,4,4a,7,8,8a hexahydro 1H isochromene; Intramolecular Diels Alder cycloaddition; Microwave; Wittig olefination

Indexed keywords

3,4,4A,7,8,8A HEXAHYDROISOCHROMEN 1 ONE; CHROMIUM DERIVATIVE; ESTER TETHERED 1,3,9, DECATRIENE DERIVATIVE; POLYENE; UNCLASSIFIED DRUG;

EID: 78649772754     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.088     Document Type: Article
Times cited : (19)

References (52)
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    • (1995) Methods of Organic Chemistry
    • Craig, D.1
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    • For thermal IMDA of ester-tethered 1,3,9-decatrienes possessing a C10-activating group, see: R.K. Boeckman Jr., and D.M. Demko J. Org. Chem. 47 1982 1789 1792
    • (1982) J. Org. Chem. , vol.47 , pp. 1789-1792
    • Boeckman Jr., R.K.1    Demko, D.M.2
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    • For IMDA of ester-tethered 1,3,9-decatrienes under Lewis acid catalysis or non-conventional conditions, see: A. Alexakis, D. Jachiet, and L. Toupet Tetrahedron 45 1989 6203 6210
    • (1989) Tetrahedron , vol.45 , pp. 6203-6210
    • Alexakis, A.1    Jachiet, D.2    Toupet, L.3
  • 30
    • 69549105964 scopus 로고    scopus 로고
    • H. Yanai, H. Ogura, and T. Taguchi Org. Biomol. Chem. 7 2009 3657 3659 For IMDA cycloaddition catalyzed by an N-protonated chiral oxazaborolidine, see:
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3657-3659
    • Yanai, H.1    Ogura, H.2    Taguchi, T.3
  • 32
    • 0035937307 scopus 로고    scopus 로고
    • For computational calculations on IMDA of ester-tethered 1,3,9-decatrienes, see: D.J. Tantillo, K.N. Houk, and M.E. Jung J. Org. Chem. 66 2001 1938 1940
    • (2001) J. Org. Chem. , vol.66 , pp. 1938-1940
    • Tantillo, D.J.1    Houk, K.N.2    Jung, M.E.3
  • 34
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    • Org. Lett. 7 2005 4547
    • (2005) Org. Lett. , vol.7 , pp. 4547
  • 47
    • 78649792887 scopus 로고    scopus 로고
    • The E- and Z-substituted diesters of the diene alcohol 13 were prepared similarly. But the results are not included here because their IMDA adducts could not be separated by flash column chromatography
    • The E- and Z-substituted diesters of the diene alcohol 13 were prepared similarly. But the results are not included here because their IMDA adducts could not be separated by flash column chromatography.
  • 51
    • 78649780232 scopus 로고    scopus 로고
    • The X-ray crystal data (excluding structure factors) of compound 24g, given in Fig. 3, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no CCDC 785558. Copy 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:
    • The X-ray crystal data (excluding structure factors) of compound 24g, given in Fig. 3, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no CCDC 785558. Copy 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 ).
  • 52
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    • The adducts 23j/24j were obtained from the triene 21j in 42% combined yield and in 90:10 dr by heating in xylene at 210 °C for 5 h as reported in Ref. 2a
    • The adducts 23j/24j were obtained from the triene 21j in 42% combined yield and in 90:10 dr by heating in xylene at 210 °C for 5 h as reported in Ref. 2a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.