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Volumn , Issue 1, 1999, Pages 37-40

Facile total synthesis of (±)-adalinine

Author keywords

Adalinine; Cyclic N,O acetals; Lewis acid induced allylation; Nitrogenated quaternary center; Piperidine alkaloid

Indexed keywords

2 PIPERIDONE DERIVATIVE; ADALININE; ALKALOID; ALLYLTRIMETHYLSILANE; PIPERIDONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032915617     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2561     Document Type: Article
Times cited : (29)

References (17)
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    • For a review of the piperidine alkaloids, see: (a) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspective, Vol. 3; Pelletier, S. W., Ed.; Wiley: New York, 1985; Ch. 1, pp. 1-90.
    • (1985) Alkaloids: Chemical and Biological Perspective , vol.3 , pp. 1-90
    • Fodor, G.B.1    Colasanti, B.2
  • 3
    • 77957037489 scopus 로고    scopus 로고
    • Pelletier, S. W., Ed.; Elsevier Science: Oxford, Ch. 2
    • (b) Schneider, M. J. In Alkaloids: Chemical and Biological Perspective, Vol. 10; Pelletier, S. W., Ed.; Elsevier Science: Oxford, 1996; Ch. 2, pp. 155-299.
    • (1996) Alkaloids: Chemical and Biological Perspective , vol.10 , pp. 155-299
    • Schneider, M.J.1
  • 5
    • 0001408338 scopus 로고    scopus 로고
    • For a recent review of the coccinellid alkaloids, see: King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105.
    • (1996) Chem. Rev. , vol.96 , pp. 1105
    • King, A.G.1    Meinwald, J.2
  • 7
    • 0026334112 scopus 로고
    • For the enantioselective construction of a quaternary center at the a position of the pyrrolidine system by Lewis acid-allylsilane alkylation of cyclic N-acyl-N,O-acetals, see: Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9858
    • Burgess, L.E.1    Meyers, A.I.2
  • 9
    • 85056013441 scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 81,161,348
    • (a) Jpn. Kokai Tokkyo Koho JP 81,161,348; Chem. Abst. 1982, 96, 142275z.
    • (1982) Chem. Abst. , vol.96
  • 13
    • 0001673091 scopus 로고
    • Heathcock, C. H., Ed.; Pergamon Press: Oxford, Ch. 4.5
    • Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Ch. 4.5, pp. 1047-1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 14
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    • note
    • The oxo compound 17 was actually isolated as a 1:1 mixture of two atropisomers i and ii, which were easily separated by (Formula presented) silica gel chromatography and assigned their relative stereochemistry as shown based on NOESY data. In this work, this mixture was used without separation in the next reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.