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Volumn 10, Issue 13, 2004, Pages 3286-3300

Double ring-closing metathesis reaction of nitrogen-containing tetraenes: Efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives

Author keywords

Alkaloids; Asymmetric synthesis; Cyclization; Heterocycles; Metathesis

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; ISOMERS; SYNTHESIS (CHEMICAL);

EID: 3142683132     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305581     Document Type: Article
Times cited : (69)

References (89)
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    • a) J. T. Wróbel in The Alkaloids, Vol, 26 (Ed.: A. Brossi), Academic Press, San Diego, 1985, pp. 327-384;
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    • (Ed.: A. Brossi), Academic Press, San Diego
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    • For reports on the synthesis of alkaloid skeletons through the ring-by-ring approach with an ring-closing metathesis reaction, see: a) C. Paolucci, L. Musiani, F. Venturelli, A. Fava, Synthesis 1997, 1415;
    • (1997) Synthesis , pp. 1415
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    • d) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012;
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    • d) J. S. Clark, O. Hamelin, Angew. Chem. 2000, 112, 380; Angew. Chem. Int. Ed. 2000, 39, 372.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 372
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    • a) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953. For the first successful RCM reaction of an acrylamide with second-generation Grubbs catalysts, see:
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    • Scholl, M.1    Ding, S.2    Lee, C.W.3    Grubbs, R.H.4
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    • note
    • Compound 9a was synthesized by treatment of allyl magnesium bromide with ethyl formate.
  • 77
    • 0001806205 scopus 로고
    • Compounds 13a and 13b were prepared by treatment of allyl magnesium bromide with acetonitrile or butyronitrile. For the procedure, see: H. R. Henze, B. B. Allen, W. B. Leslie, J. Am. Chem. Soc. 1943, 65, 87.
    • (1943) J. Am. Chem. Soc. , vol.65 , pp. 87
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    • note
    • int = 0.1721), not observed (I > 2σ(I)) 1658, parameters 163. CCDC-172850 contains the supplementary crystallographic data for 15a. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336033; or deposit@ccdc.cam.uk).
  • 80
    • 3142684597 scopus 로고    scopus 로고
    • note
    • 2. These data can be obtained as described in ref. [22].
  • 83
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    • a) J. A. Rao, M. P. Cava, J. Org. Chem. 1989, 54, 2751; (Z)-2,5-dihexen-1-ol (cis/trans = 99:1, determined by GC analysis) was prepared by the reduction of hex-2-yn-5-en-1-ol with the Zn-Cu couple in methanol (sealed tube, 120°C) in 80% yield.
    • (1989) J. Org. Chem. , vol.54 , pp. 2751
    • Rao, J.A.1    Cava, M.P.2
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    • note
    • Direct monobenzylation of (3R,4S) diene 23 yielded two benzyl ethers with a low selectivity [Eq. (1)]. (Equation presented).
  • 85
    • 3142741706 scopus 로고    scopus 로고
    • note
    • 19F NMR spectrum of these Mosher's esters.
  • 86
    • 3142722652 scopus 로고    scopus 로고
    • note
    • int = 0.0516), not observed (I > 2σ(I)) 1941, parameters 204. CCDC-218925 contains the supplementary crystallographic data for 36. These data can be obtained as described in ref. [22].
  • 87
    • 3142743221 scopus 로고    scopus 로고
    • note
    • Compound 12d was prepared according to Equation (2). (Equation presented).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.