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Volumn , Issue 13, 2004, Pages 2840-2847

Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation: Synthesis of (±)-isoretronecanol

Author keywords

Alkaloids; Allylic alkylation; Palladium; Synthetic methods

Indexed keywords

ALKADIENE; INDOLE DERIVATIVE; PALLADIUM; PYRROLIZIDINE ALKALOID;

EID: 4544291862     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400135     Document Type: Article
Times cited : (35)

References (65)
  • 2
    • 33947588727 scopus 로고
    • (Ed.: A. Brossi), Academic Press, San Diego, chapter 7
    • [1b] J. T. Wróbel, in The Alkaloids: Chemistry and Pharmacology (Ed.: A. Brossi), Academic Press, San Diego, 1985; vol 26, chapter 7, p. 327.
    • (1985) The Alkaloids: Chemistry and Pharmacology , vol.26 , pp. 327
    • Wróbel, J.T.1
  • 26
    • 0008371590 scopus 로고
    • [3c] S. Takano, N. Ogawa, K. Ogasawara, Heterocycles 1981, 16, 915-919. See also: refs.[2a,2b,2p,2r,2s] The enantiomer of the alkaloid laburnine is trachelanthamidine. See also refs2a2b2p2r2s The enantiomer of the alkaloid laburnine is trachelanthamidine.
    • (1981) Heterocycles , vol.16 , pp. 915-919
    • Takano, S.1    Ogawa, N.2    Ogasawara, K.3
  • 39
    • 0032880098 scopus 로고    scopus 로고
    • Synthesis of the hexahydroindol-2-one skeleton: [7a] H. Ishibashi, A. Toyao, Y. Takena, Synlett 1999, 9, 1468-1470.
    • (1999) Synlett , vol.9 , pp. 1468-1470
    • Ishibashi, H.1    Toyao, A.2    Takena, Y.3
  • 48
    • 33748495584 scopus 로고    scopus 로고
    • Support for such an assignment comes from analysis of the coupling constant values observed in our previous work[6a] and those reported in the literature for structurally related molecules. See: [12a] M. Ikeda, H. Teranishi, K. Nozaki, H. Ishibashi, J. Chem. Soc., Perkin Trans. 1 1998, 1691-1698.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1691-1698
    • Ikeda, M.1    Teranishi, H.2    Nozaki, K.3    Ishibashi, H.4
  • 58
    • 85077854948 scopus 로고
    • For reviews see: [19a] A. P. Krapcho, Synthesis 1982, 805-822.
    • (1982) Synthesis , pp. 805-822
    • Krapcho, A.P.1
  • 60
    • 4544302768 scopus 로고    scopus 로고
    • note
    • In the presently studied route (±)-12a is obtained in five steps starting from 1,3-cyclohexadiene, with a 65% overall yield.
  • 65
    • 4544265405 scopus 로고    scopus 로고
    • note
    • The stereochemistry of 1 has been checked by NOE experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.