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Volumn 63, Issue 51, 2007, Pages 12639-12645

Sequential pericyclic reaction of ene-diallene: synthesis of (±)-estrone

Author keywords

4+2 Cycloaddition; Allenes; Estrone; Tandem reaction

Indexed keywords

ALLENE DERIVATIVE; ENE DIALLENE; ESTRONE; PERHYDROPHENANTHRENE DERIVATIVE; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG;

EID: 35748948080     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.008     Document Type: Article
Times cited : (19)

References (60)
  • 3
    • 35748966577 scopus 로고    scopus 로고
    • The tandem formation and intramolecular [4+2] cycloaddition of 1-sulfinyl-1-vinylallenes, triggered by [2,3]-sigmatropic rearrangement of the corresponding propargyl sulfenates, have been reported:
  • 23
    • 0030005845 scopus 로고    scopus 로고
    • The intermolecular cycloaddition reaction of the o-quinodimethane derived from cis-4-octene-2,6-diyne-1,8-diol and PhSCl was described in the review article by Grissom:
    • The intermolecular cycloaddition reaction of the o-quinodimethane derived from cis-4-octene-2,6-diyne-1,8-diol and PhSCl was described in the review article by Grissom:. Grissom J.W., Gunawardena G.U., Klingberg D., and Huang D. Tetrahedron 52 (1996) 6453-6518
    • (1996) Tetrahedron , vol.52 , pp. 6453-6518
    • Grissom, J.W.1    Gunawardena, G.U.2    Klingberg, D.3    Huang, D.4
  • 24
    • 35748943994 scopus 로고    scopus 로고
    • [1,5] Hydrogen-shifted product was isolated as 8′ in 29% yield after m-CPBA oxidation of a mixture of pericyclic reaction products: Kitagaki, S.; Ohdachi, K.; Mukai, C. Unpublished results. {A figure is presented}
  • 28
    • 35748951485 scopus 로고    scopus 로고
    • For reviews on total syntheses of estrogens, see:
  • 43
    • 35748970346 scopus 로고    scopus 로고
    • note
    • The use of t-butyl acrylate as a Michael acceptor led to increase in stereoselectivity as well as chemical yield of the desired product compared to the reported procedure; stereoselectivity: trans/cis=6.5:1, isolated yield of trans isomer: 66%. See Ref. 12c.
  • 44
    • 35748983072 scopus 로고    scopus 로고
    • note
    • The product was obtained as a separable mixture of diastereoisomers in a ratio of 5:1 and the desired stereoisomer was used for the next reaction. Their stereochemical assignments were unambiguously established by the NOE experiments.
  • 47
    • 35748930747 scopus 로고    scopus 로고
    • note
    • 13C NMR analyses.
  • 48
    • 35748958280 scopus 로고    scopus 로고
    • note
    • The diastereomer ratio was not determined.
  • 50
    • 35748951172 scopus 로고    scopus 로고
    • For Baeyer-Villiger oxidation of C-3 acetyl steroids, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.