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Volumn 45, Issue 19, 2004, Pages 3783-3786

Stereocontrolled synthesis of quinine and quinidine

Author keywords

Cyclopentene 1,3 diol monoacetate; Epoxide ring opening; Piperidine; Quinidine; Quinine

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE; CYCLOPENTENE DERIVATIVE; EPOXIDE; PIPERIDINE; QUINIDINE; QUININE;

EID: 1942424997     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.085     Document Type: Article
Times cited : (68)

References (64)
  • 2
    • 0030058445 scopus 로고    scopus 로고
    • List A.F. Leukemia. 10:1996;937-942.
    • (1996) Leukemia , vol.10 , pp. 937-942
    • List, A.F.1
  • 22
    • 0015516865 scopus 로고
    • Similar quinuclidine formations from epoxides have been reported:
    • Similar quinuclidine formations from epoxides have been reported: Grethe G., Gutzwiller J., Lee H.L., Uskokovic M.R. Helv. Chim. Acta. 55:1972;1044-1047.
    • (1972) Helv. Chim. Acta , vol.55 , pp. 1044-1047
    • Grethe, G.1    Gutzwiller, J.2    Lee, H.L.3    Uskokovic, M.R.4
  • 26
    • 1942535518 scopus 로고    scopus 로고
    • see Refs. 4a,5,7c
    • Olefin 5 has been reported to afford a mixture of 9-deoxy-quinine 3 and the C(8)-epimer in ∼1:1 ratio: (a) see Refs. 4a,5,7c;
  • 58
    • 1942535519 scopus 로고    scopus 로고
    • note
    • Ozonolysis in MeOH proceeded with somewhat lower product selectivity.
  • 60
    • 1942503695 scopus 로고    scopus 로고
    • note
    • 2 under similar conditions was unsuccessful.
  • 61
    • 1942503694 scopus 로고    scopus 로고
    • note
    • An attempted conversion of the N-benzoyl piperidine alcohol i, prepared from 13 by the sequence shown below, into selenide ii was unsuccessful in our hand.
  • 64
    • 1942535517 scopus 로고    scopus 로고
    • note
    • 3) for epoxide 19 and its diastereomer synthesized through oxidation with AD-mix-α are δ 4.15 (d, J=1.8 Hz) and 4.17 (d, J=1.8 Hz), respectively, for proton at C(9).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.