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Volumn 48, Issue 12, 2009, Pages 2228-2230

Stereoselective synthesis of enantiomerically pure nupharamine alkaloids from castoreum

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Domino reactions; Indolizidines; Terpenoids

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL AUXILIARIES; DOMINO REACTIONS; INDOLIZIDINES; TERPENOIDS;

EID: 61949178196     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805606     Document Type: Article
Times cited : (33)

References (32)
  • 2
    • 77957025825 scopus 로고
    • Ed, R. H. F. Manske, Academic Press, New York
    • a) J. T. Wróbel in The Alkaloids, Vol. 9 (Ed.: R. H. F. Manske), Academic Press, New York, 1967, pp. 441-465;
    • (1967) The Alkaloids , vol.9 , pp. 441-465
    • Wróbel, J.T.1
  • 3
    • 77957099034 scopus 로고
    • Ed, R. H. F. Manske, Academic Press, New York
    • b) J. T. Wróbel in The Alkaloids, Vol. 16 (Ed.: R. H. F. Manske), Academic Press, New York, 1977, pp. 181.
    • (1977) The Alkaloids , vol.16 , pp. 181
    • Wróbel, J.T.1
  • 4
    • 61949384382 scopus 로고    scopus 로고
    • Teubner, Stuttgart
    • E. Breitmaier in Alkaloide, Teubner, Stuttgart, 2002, p. 45.
    • (2002) Alkaloide , pp. 45
    • Breitmaier, E.1
  • 29
    • 61949235892 scopus 로고    scopus 로고
    • Spectroscopic data of 3: 1H NMR (400 MHz, CDCl 3, δ, 7.35-7.31 (m, 2H, furyl-5, furyl-2, 6.43 (s br, 1H, furyl-4, 2.91-2.82 (m, 2H, H-5ax, H-3 a,ax, 2.15-2.06 (m, 1H, H-8a,ax, 1.97-1.89 (m, 1H, H-8eq, 1.88-1.75 (m, 2H, H-3b,eq, H-6a,ax, 1.71-1.53 (m, 6H, H-7a,b, H-1a,b H-2a,b, 1.52-1.45 (m, 1H, H-6b,eq, 1.04 ppm (d, 3J, 7.0, 3H, CH3, 13C NMR (100.6 MHz, CDCl3, δ, 142.58 (furyl-5, 139.06 (furyl-2, 128.70 (furyl-3, 109.71 (furyl-4, 67.54 (C-8a, 60.91 (C-5, 53.40 (C-3, 32.14 (C-1, 29.42 (C-8, 28.92 (C-6, 26.84 (C-7, 20.06 (C-2, 12.19 ppm (CH3, ESI-MS (pos, 206.16, M+H, calcd. 206.15, HR ESI-MS pos, 206.1552, M+H, calcd. 206.1545
    • +, calcd. 206.1545).
  • 30
    • 61949473264 scopus 로고    scopus 로고
    • Addition of the protonating reagent at -95°C increased the diastereomeric ratio to 93:7.
    • Addition of the protonating reagent at -95°C increased the diastereomeric ratio to 93:7.
  • 31
    • 61949112170 scopus 로고    scopus 로고
    • Spectroscopic data of 4: 1H NMR (400 MHz, CDCl 3, δ, 7.35 (m, 2H, furyl-5, furyl-2, 6.47 (sbr, 1H, furyl-4, 2.99-2.78 (m, 2H, H-3a, H-5, 2.01-1.90 (m, 2H, H-1a, H-3b, 1.84-1.70 (m, 3H, H-7a, H-6 a,b, 1.68-1.55 (m, 3H, H-2a,b, H-8a, 1.54-1.36 (m, 2H, H-1b, H-8, 1.14-1.01 (m, 1H, H-7b, 0.91 (d, 3J, 6.5, 3H, CH3, 13C NMR (100.6 MHz, CDCl3, 142.75 (furyl-5, 139.38 (furyl-2, 128.01 (furyl-3, 109.73 (furyl-4, 71.50 (C-8a, 59.81 (C-5, 53.09 (C-3, 36.25 (C-8, 33.99 (C-6, 33.83 (C-7, 28.97 (C-1, 20.03 (C-2, 18.82 ppm (CH3, ESI-MS (pos, 206.16, M+H, calcd. 206.15, HR ESI-MS pos, 206.1539, M+H, calcd. 206.1545
    • +, calcd. 206.1545).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.