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Volumn 12, Issue 12, 2010, Pages 2738-2741

Total synthesis of 7,11-cyclobotryococca-5,12,26-triene using an oxidative radical cyclization as a key step

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EID: 77953558234     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100794k     Document Type: Article
Times cited : (31)

References (64)
  • 2
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    • note
    • 30 unsaturated hydrocarbon with the same carbon skeleton as 7,11-cyclobotryococca-5,12,26-triene may have previously been isolated. See: ref 1 and Requejo, A. G.; Quinn, J. G. Geochim. Cosmochim. Acta 1983, 47, 1075-1090
    • (1983) Geochim. Cosmochim. Acta , vol.47 , pp. 1075-1090
    • Requejo, A.G.1    Quinn, J.G.2
  • 3
    • 70349443542 scopus 로고    scopus 로고
    • For discussions concerning the biosynthesis of 1 see ref 1 and
    • For discussions concerning the biosynthesis of 1 see ref 1 and Pan, J.-J.; Bugni, T. S.; Poulter, C. D. J. Org. Chem. 2009, 74, 7562-7565
    • (2009) J. Org. Chem. , vol.74 , pp. 7562-7565
    • Pan, J.-J.1    Bugni, T.S.2    Poulter, C.D.3
  • 4
    • 77953595484 scopus 로고    scopus 로고
    • For reviews on the asymmetric synthesis of all carbon quaternary stereocenters see
    • For reviews on the asymmetric synthesis of all carbon quaternary stereocenters see
  • 7
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    • Fuji, K. Chem. Rev. 1993, 93, 2037-2066
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 10
    • 77953606575 scopus 로고    scopus 로고
    • For reviews of the use of manganese(III) acetate in organic synthesis see
    • For reviews of the use of manganese(III) acetate in organic synthesis see
  • 16
    • 77953597592 scopus 로고    scopus 로고
    • For the use of copper(II) triflate in conjunction with manganese(III) acetate, see
    • For the use of copper(II) triflate in conjunction with manganese(III) acetate, see
  • 20
    • 77953548495 scopus 로고    scopus 로고
    • For the synthesis of γ-lactones using (a) manganese(III) acetate and copper(II) acetate see
    • For the synthesis of γ-lactones using (a) manganese(III) acetate and copper(II) acetate see
  • 27
    • 72149130393 scopus 로고
    • Ed.; Wiley: New York
    • Kochi, J. K. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 1, pp 594 - 623.
    • (1973) Free Radicals , vol.1 , pp. 594-623
    • Kochi, J.K.1    Kochi, J.K.2
  • 28
    • 77953575777 scopus 로고    scopus 로고
    • note
    • This reaction was conducted on ca. 1 g scale. On a smaller scale (ca. 300 mg), the yield can be as high as 90%.
  • 36
    • 77953574176 scopus 로고    scopus 로고
    • For a review on the Synthesis of highly substituted olefins see
    • For a review on the Synthesis of highly substituted olefins see
  • 38
    • 77953549508 scopus 로고    scopus 로고
    • For a recent example of difficulty encountered when using a Wittig reaction to form a trisubstituted olefin see
    • For a recent example of difficulty encountered when using a Wittig reaction to form a trisubstituted olefin see
  • 40
    • 77953589694 scopus 로고    scopus 로고
    • For a recent example of competitive hydrometallation of a terminal olefin in the presence of an internal acetylene see
    • For a recent example of competitive hydrometallation of a terminal olefin in the presence of an internal acetylene see
  • 47
    • 77953563303 scopus 로고    scopus 로고
    • For recent examples in natural product synthesis see
    • For recent examples in natural product synthesis see
  • 53
    • 77953582875 scopus 로고    scopus 로고
    • For a review on organocopper chemistry see
    • For a review on organocopper chemistry see
  • 55
    • 77953600137 scopus 로고    scopus 로고
    • This is the procedure described by Monte and Lindbeck
    • This is the procedure described by Monte and Lindbeck
  • 57
    • 77953598535 scopus 로고    scopus 로고
    • note
    • 1H NMR of the coupled product 2 did not indicate the presence of any other alkene diastereomers.
  • 60
    • 77953575461 scopus 로고    scopus 로고
    • We followed the procedure of Uguen and co-worker for the preparation of the allylic alcohol 22 from the acetylene 19
    • We followed the procedure of Uguen and co-worker for the preparation of the allylic alcohol 22 from the acetylene 19
  • 62
    • 77953608320 scopus 로고    scopus 로고
    • note
    • The assignment of the structures 23 and 24 is only tentative as isolation of pure compounds was not possible. The formation of 23 and 24 may be due to the formation of isomeric allylic chlorides in the previous step.
  • 63
    • 77953565840 scopus 로고    scopus 로고
    • Further purification provided pure 1
    • Further purification provided pure 1.
  • 64
    • 77953579174 scopus 로고    scopus 로고
    • 13C NMR resonance is quoted at δ = 25.79 ppm, whereas in the original spectra, and the spectra of the synthetic material, C-15 resonates at δ = 24.80 ppm
    • 13C NMR resonance is quoted at δ = 25.79 ppm, whereas in the original spectra, and the spectra of the synthetic material, C-15 resonates at δ = 24.80 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.