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Volumn 70, Issue 25, 2005, Pages 10368-10374

Diastereoselective intramolecular α-amidoalkylation reactions of L-DOPA derivatives. Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; REACTION KINETICS; STEREOCHEMISTRY;

EID: 28744436180     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051584w     Document Type: Article
Times cited : (48)

References (44)
  • 1
    • 46549103031 scopus 로고
    • For reviews on N-acyliminium ion chemistry, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
    • (1985) Tetrahedron , vol.41 , pp. 4367-4416
    • Speckamp, W.N.1    Hiemstra, H.2
  • 2
    • 77957077000 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, pp 271-339.
    • (1988) The Alkaloids , vol.32 , pp. 271-339
    • Hiemstra, H.1    Speckamp, W.N.2
  • 3
    • 0001673091 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (c) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 4
    • 0001513757 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart, Workbench ed. E21
    • (d) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl]; Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Workbench ed. E21, Vol. 3, pp 1952-2010.
    • (1996) Stereoselective Synthesis [Houben-Weyl] , vol.3 , pp. 1952-2010
    • De Koning, H.1    Speckamp, W.N.2
  • 9
    • 0033986185 scopus 로고    scopus 로고
    • For reviews, see ref 1. For some selected examples of diastereoselective intramolecular α-amidoalkylation reactions of cyclic N-acyliminium ions, see the following references. Steric control by the substituents in the ring: (a) Ostendorf, M.; van der Neut, S.; Rutjes, F. P. J. T.; Hiemstra, H. Eur. J. Org. Chem. 2000, 65, 115-124.
    • (2000) Eur. J. Org. Chem. , vol.65 , pp. 115-124
    • Ostendorf, M.1    Van Der Neut, S.2    Rutjes, F.P.J.T.3    Hiemstra, H.4
  • 33
    • 2442698345 scopus 로고    scopus 로고
    • Transl. Khim. Geterotsikl. Soedin
    • Pyrrolo[2,1-a]isoquinolones have attracted considerable interest because they possess antidepressant, muscarinic agonist, antiplatelet, and anticancer activity. Moreover, they can be used as PET radiotracers for imaging serotonin uptake sites. The importance of these nitrogen heterocycles is further enhanced by their utility as advanced intermediates for the synthesis of alkaloids. For a general review on properties, synthesis, and reactivity of pyrrolo[2,1-a] isoquinolines, see: Mikhailovskii, A. G.; Shklyaev, V. S. Chem. Heterocycl. Compd. 1997, 33, 243-265; Transl. Khim. Geterotsikl. Soedin.
    • (1997) Chem. Heterocycl. Compd. , vol.33 , pp. 243-265
    • Mikhailovskii, A.G.1    Shklyaev, V.S.2
  • 34
    • 28744432715 scopus 로고    scopus 로고
    • note
    • O-Silylation of 4 was carried out with imidazole and TBDPSCl to give 5a in excellent yield (95%). However, the yields of the benzyl and methyl ethers 5b and 5c were only moderate due to the formation of side products 6 (35%) and 7 (30%), respectively. Several attempts to improve these yields failed. See Supporting Information.
  • 35
    • 0029919982 scopus 로고    scopus 로고
    • The use of 1, 2, or 3 equiv of MeLi led to lower yields of the oxoamides and starting material. The requirement of more than stoichiometric amounts of organolithiums has been attributed to coordination of the organolithium to oxygenated groups. See: Sardina, F. J.; Blanco, M. J. Org. Chem. 1996, 61, 4748-4755.
    • (1996) J. Org. Chem. , vol.61 , pp. 4748-4755
    • Sardina, F.J.1    Blanco, M.2
  • 36
    • 28744434072 scopus 로고    scopus 로고
    • note
    • All enantiomeric excesses were checked by chiral stationary phase HPLC by comparison with the corresponding racemates, obtained by analogous routes from racemic D,L-DOPA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.