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Volumn 2, Issue 26, 2000, Pages 4205-4208

Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMIDE; AZOCINE DERIVATIVE; CYTISINE; QUINOLIZINE DERIVATIVE;

EID: 0034727939     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006765t     Document Type: Article
Times cited : (76)

References (71)
  • 2
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    • Structure determination
    • (b) Structure determination: Ing, H. R. J. Chem. Soc. 1932, 2778.
    • (1932) J. Chem. Soc. , pp. 2778
    • Ing, H.R.1
  • 6
    • 0041292868 scopus 로고    scopus 로고
    • (d) Eur. J. Pharmacol. 2000, 393, Issues 1-3, 1-340.
    • (2000) Eur. J. Pharmacol. , vol.393 , Issue.1-3 , pp. 1-340
  • 12
    • 37049148123 scopus 로고
    • See also, refs 6-8
    • Ing, H. R. J. Chem. Soc. 1931, 2195. See also, refs 6-8.
    • (1931) J. Chem. Soc. , pp. 2195
    • Ing, H.R.1
  • 20
    • 0000799110 scopus 로고    scopus 로고
    • This alcohol is readily available as described. See: (a) Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1984, 49, 928-931; Org. Synth. 1997, 75, 195-200.
    • (1984) J. Org. Chem. , vol.49 , pp. 928-931
    • Deprés, J.-P.1    Greene, A.E.2
  • 21
    • 0000799110 scopus 로고    scopus 로고
    • This alcohol is readily available as described. See: (a) Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1984, 49, 928-931; Org. Synth. 1997, 75, 195-200.
    • (1997) Org. Synth. , vol.75 , pp. 195-200
  • 48
    • 0000702671 scopus 로고
    • Wiley: New York
    • Heck, R. F. In Organic Reactions; Wiley: New York, 1982; Vol. 27, p 345.
    • (1982) Organic Reactions , vol.27 , pp. 345
    • Heck, R.F.1
  • 49
    • 0042294676 scopus 로고    scopus 로고
    • note
    • The recovered yield of 5 was not enhanced when chromatographically pure 3c was employed.
  • 50
    • 0041793535 scopus 로고    scopus 로고
    • note
    • 3 tube) progressed rapidly, albeit causing decomposition of the air-sensitive cycloadduct and vinyl Heck intermediate. This observation suggests that catalytic oxygen is required to generate the active palladium catalyst.
  • 57
    • 0023234722 scopus 로고
    • Without pyridine, see: Nomura, K.; Okazaki, K.; Hori, K.; Yoshii, E. J. Am. Chem. Soc. 1987, 109, 3402-3408. With pyridine, see: (a) Ray, R.; Matteson, D. S. Tetrahedron Lett. 1980, 21, 449-450.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3402-3408
    • Nomura, K.1    Okazaki, K.2    Hori, K.3    Yoshii, E.4
  • 58
    • 0000278459 scopus 로고
    • Without pyridine, see: Nomura, K.; Okazaki, K.; Hori, K.; Yoshii, E. J. Am. Chem. Soc. 1987, 109, 3402-3408. With pyridine, see: (a) Ray, R.; Matteson, D. S. Tetrahedron Lett. 1980, 21, 449-450.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 449-450
    • Ray, R.1    Matteson, D.S.2
  • 60
    • 0004169871 scopus 로고
    • Wiley: New York, Chapter 3
    • (a) Emerson, W. S. In Organic Reactions; Wiley: New York, 1982; Vol. 4, Chapter 3.
    • (1982) Organic Reactions , vol.4
    • Emerson, W.S.1
  • 70
    • 0042294635 scopus 로고    scopus 로고
    • An efficient resolution is known. See ref 6
    • An efficient resolution is known. See ref 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.