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Volumn 46, Issue 37, 2005, Pages 6381-6384

Improved synthesis of quinine alkaloids with the Teoc protective group

Author keywords

CsF; Nitrogen atom; Protective group; Quinidine; Quinine; Teoc

Indexed keywords

ALKALOID DERIVATIVE; CESIUM FLUORIDE; FLUORINE DERIVATIVE; PROTECTIVE AGENT; QUINIDINE; QUININE; QUINUCLIDINE; UNCLASSIFIED DRUG;

EID: 23744485746     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.171     Document Type: Article
Times cited : (39)

References (25)
  • 2
    • 0034829787 scopus 로고    scopus 로고
    • Stork's approach to quinine seems inapplicable to that of quinidine, and Jacobsen's synthesis of the quinine alkaloids suffer from low stereoselectivity in the preparation of the piperidine ring: G. Stork, D. Niu, R.A. Fujimoto, E.R. Koft, J.M. Balkovec, J.R. Tata, and G.R. Dake J. Am. Chem. Soc. 123 2001 3239 3242
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3239-3242
    • Stork, G.1    Niu, D.2    Fujimoto, R.A.3    Koft, E.R.4    Balkovec, J.M.5    Tata, J.R.6    Dake, G.R.7
  • 13
    • 0000081229 scopus 로고
    • 5e) seemed incompatible with our strategy for synthesis of the quinine alkaloids due to hard conditions, instability of the protective group as such, and/or inconvenience of the reagent T.A. Montzka, J.D. Matiskella, and R.A. Partyka Tetrahedron Lett. 1974 1325 1327
    • (1974) Tetrahedron Lett. , pp. 1325-1327
    • Montzka, T.A.1    Matiskella, J.D.2    Partyka, R.A.3
  • 18
    • 33645194516 scopus 로고    scopus 로고
    • note
    • 2b
  • 21
    • 33645207271 scopus 로고    scopus 로고
    • note
    • 7b
  • 23
    • 33645207498 scopus 로고    scopus 로고
    • note
    • 7a solid triphosgene was studied to carry out the reaction in a safer way.
  • 24
    • 33645202865 scopus 로고    scopus 로고
    • note
    • 4, filtered, and concentrated in vacuo. Chromatography of the residue (hexane/EtOAc = 10:1) afforded the desired product 10 (47 mg, 99%).
  • 25
    • 33645206258 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy and TLC analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.