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Volumn 46, Issue 40, 2007, Pages 7671-7673

Total synthesis of (+)-fawcettimine

Author keywords

(+) fawcettimine; Alkaloids; Cyclization; Gold; Total synthesis

Indexed keywords

ALKALOIDS; FAWCETTIMINES;

EID: 35048843654     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702695     Document Type: Article
Times cited : (145)

References (34)
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    • For recent reviews of gold(I)-catalyzed reactions, see: a) E. Jiménez-Nunez, A. M. Echavarren, Chem. Commun. 2007, 333;
    • For recent reviews of gold(I)-catalyzed reactions, see: a) E. Jiménez-Nunez, A. M. Echavarren, Chem. Commun. 2007, 333;
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    • Iodide 11 was prepared by iodination of 5-methylcyclohexen-3-one using the method reported in R. Benhida, P. Blanchard, J.-L. Fourrey, Tetrahedron Lett. 1998, 39, 6849.
    • Iodide 11 was prepared by iodination of 5-methylcyclohexen-3-one using the method reported in R. Benhida, P. Blanchard, J.-L. Fourrey, Tetrahedron Lett. 1998, 39, 6849.
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    • for the synthesis of the allenyltributyltin reagent, see
    • for the synthesis of the allenyltributyltin reagent, see: Y. Ueno, M. Okawara, J. Am. Chem. Soc. 1979, 101, 1893.
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 1893
    • Ueno, Y.1    Okawara, M.2
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    • We propose that the reactivity of 15c might derive from intramolecular coordination of the alkene to palladium. This interaction results in occupation of the vacant site on the metal center, which is required for the β-hydride elimination that ulitmately leads to reduction of the vinyliodide.
    • We propose that the reactivity of 15c might derive from intramolecular coordination of the alkene to palladium. This interaction results in occupation of the vacant site on the metal center, which is required for the β-hydride elimination that ulitmately leads to reduction of the vinyliodide.
  • 31
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    • For additional examples of cross-coupling with 15c, see Table 1 in the Supporting Information.
    • For additional examples of cross-coupling with 15c, see Table 1 in the Supporting Information.
  • 33
    • 35048883058 scopus 로고    scopus 로고
    • Synthetic 1: [α]DRT, 89 deg cm 3 g-1 dm-1 (c, 0.55 g cm-3, MeOH, natural 1: [α]DRT, 91 deg cm 3 g-1 dm-1 (c, 0.66 g cm-3, MeOH, We thank Prof. Da-Yuan Zhu (Shanghai Institute of Materia Medica, Chinese Academy of Science) for providing us with the optical rotation of natural fawcettimine
    • -3, MeOH). We thank Prof. Da-Yuan Zhu (Shanghai Institute of Materia Medica, Chinese Academy of Science) for providing us with the optical rotation of natural fawcettimine.
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    • 35048891167 scopus 로고    scopus 로고
    • For a review on organocatalysis in the synthesis of natural products, see
    • For a review on organocatalysis in the synthesis of natural products, see: R. Marcia de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575.
    • (2007) Eur. J. Org. Chem , pp. 2575
    • Marcia de Figueiredo, R.1    Christmann, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.