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Volumn 11, Issue 21, 2009, Pages 4930-4933

Stereocontrolled generation of the (2R) chroman core of vitamin E: Total synthesis of (2R,4'RS,8'RS)-α-tocopherol

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA TOCOPHEROL; CHROMAN DERIVATIVE;

EID: 70350623198     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9020783     Document Type: Article
Times cited : (27)

References (52)
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    • Gunstone, F. P., Ed.; Academic Press: Sheffield, U.K.
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    • (1999) Lipid Synthesis and Manufacture , pp. 250-267
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  • 19
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    • Shen, H.C.1
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    • 34447099395 scopus 로고    scopus 로고
    • Litwack, G., Ed.; Elsevier: San Diego
    • Reviews: (a) Netscher, T. In Vitamins and Hormones; Litwack, G., Ed.; Elsevier: San Diego, 2007; Vol.76, pp 155-202.
    • (2007) Vitamins and Hormones , vol.76 , pp. 155-202
    • Netscher, T.1
  • 23
    • 0001069947 scopus 로고    scopus 로고
    • (d) Netscher, T. Chimia 1996, 50, 563-567. Recent references:
    • (1996) Chimia , vol.50 , pp. 563-567
    • Netscher, T.1
  • 33
  • 39
    • 0000917197 scopus 로고
    • Compound 6 was prepared in two steps (see Supporting Information) from commercially available trimethyl hydroquinone following a modification of a previously described procedure:Harada, T.; Hayashiya, T.; Wada, I.; Iwa-ake, N.; Oku, A. J. Am. Chem. Soc. 1987, 109, 527-532.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 527-532
    • Harada, T.1    Hayashiya, T.2    Wada, I.3    Iwa-ake, N.4    Oku, A.5
  • 42
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    • 4
    • 4.
  • 43
    • 70350646548 scopus 로고    scopus 로고
    • CCDC 730815 for (S,SS)-10 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
    • CCDC 730815 for (S,SS)-10 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
  • 47
    • 70350635144 scopus 로고    scopus 로고
    • When the same reaction was performed in absence of microwave irradiation, compound 2 was isolated pure in 48% yield
    • When the same reaction was performed in absence of microwave irradiation, compound 2 was isolated pure in 48% yield.
  • 49
    • 1842689070 scopus 로고    scopus 로고
    • For a few examples of ring-closing metathesis chemistry applied to sulfoxides, see: (b) Bates, D. K.; Li, X.; Jog, P. V. J. Org. Chem. 2004, 69, 2750-2754.
    • (2004) J. Org. Chem. , vol.69 , pp. 2750-2754
    • Bates, D.K.1    Li, X.2    Jog, P.V.3
  • 52
    • 70350626529 scopus 로고    scopus 로고
    • (2S,4'RS,8'RS) = 13.4 min]
    • (2S,4'RS,8'RS) = 13.4 min].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.