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Volumn 76, Issue 12, 2011, Pages 5026-5035

Synthesis of the stenine ring system from pyrrole

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOCARBONYLATION; DIASTEREOSELECTIVE; ELECTRON-RICH; RING SYSTEMS; SONOGASHIRA COUPLING; STEMONA ALKALOIDS;

EID: 79958816187     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200699k     Document Type: Article
Times cited : (44)

References (68)
  • 31
    • 79958800135 scopus 로고    scopus 로고
    • Attempts to protect the aldehyde as a dioxolane were uniformly low yielding
    • Attempts to protect the aldehyde as a dioxolane were uniformly low yielding.
  • 34
    • 79958785052 scopus 로고    scopus 로고
    • Further studies on the trichloromethylketone were not carried out as, in previous work and in model studies, we have been unable to achieve Sonogashira coupling in the presence of this functional group
    • Further studies on the trichloromethylketone were not carried out as, in previous work and in model studies, we have been unable to achieve Sonogashira coupling in the presence of this functional group.
  • 36
    • 70449449855 scopus 로고    scopus 로고
    • For a recent example of a pyrrole Sonogashira reaction, see
    • For a recent example of a pyrrole Sonogashira reaction, see: Gracia, S.; Métay, E.; Pellet-Rostaing, S.; Lemaire, M. Synlett 2009, 2617
    • (2009) Synlett , pp. 2617
    • Gracia, S.1    Métay, E.2    Pellet-Rostaing, S.3    Lemaire, M.4
  • 41
    • 79958864179 scopus 로고    scopus 로고
    • The structure, including stereochemistry, of this bromide was confirmed by X-ray crystallography
    • The structure, including stereochemistry, of this bromide was confirmed by X-ray crystallography.
  • 42
    • 0001662416 scopus 로고
    • The direct conversion of silyl ethers to bromides has been reported
    • The direct conversion of silyl ethers to bromides has been reported: Mattes, H.; Benezra, C. Tetrahedron Lett. 1987, 28, 1697
    • (1987) Tetrahedron Lett. , vol.28 , pp. 1697
    • Mattes, H.1    Benezra, C.2
  • 45
    • 79958804030 scopus 로고    scopus 로고
    • Similar results were obtained using Dowex 50WX2
    • Similar results were obtained using Dowex 50WX2.
  • 48
    • 79958853685 scopus 로고    scopus 로고
    • Details have been deposited with the Cambridge Crystallographic Data Centre and may be obtained at. CCDC deposition numbers: 13a 810121, 19 809925, 2 809926, and 26 822904
    • Details have been deposited with the Cambridge Crystallographic Data Centre and may be obtained at http://www.ccdc.cam.ac.uk. CCDC deposition numbers: 13a 810121, 19 809925, 2 809926, and 26 822904.
  • 59
    • 0000171099 scopus 로고    scopus 로고
    • Whether the active ruthenium species is mononuclear or multinuclear is unclear (;;;) but Takahashi (ref 54) proposes that it remains trinuclear
    • Whether the active ruthenium species is mononuclear or multinuclear is unclear (Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am., Chem. Soc. 1996, 118, 493) but Takahashi (ref 54) proposes that it remains trinuclear
    • (1996) J. Am., Chem. Soc. , vol.118 , pp. 493
    • Chatani, N.1    Fukuyama, T.2    Kakiuchi, F.3    Murai, S.4
  • 67
    • 79958824845 scopus 로고    scopus 로고
    • Isomer 25 may be converted completely into the stenine skeleton 2 by treatment with KO t -Bu
    • Isomer 25 may be converted completely into the stenine skeleton 2 by treatment with KO t -Bu.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.