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Volumn 65, Issue 4, 2000, Pages 1022-1030

Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; QUINAZOLINE DERIVATIVE;

EID: 0034712334     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9914364     Document Type: Article
Times cited : (92)

References (34)
  • 1
    • 0342432532 scopus 로고    scopus 로고
    • note
    • Abbreviations: Ala = Alanine, EDC = 1-ethyl-3-(3-(diethylamino)-propyl)carbodiimide·HCl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl, Gly = glycine, Phe = phenylalanine, PyBrOP = bromo-tris-pyrrolidinophosphonium hexafluorophosphate, Trp = tryptophan, Val = valine.
  • 2
    • 0032413665 scopus 로고    scopus 로고
    • For recent reviews, see (a) Michael, J. P. Nat. Prod. Rep. 1998, 15, 595-606. (b) Johne, S. In Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd edition); Ansell, M. F., Ed.; Elsevier: Amsterdam, 1995; Vol. IV I/J, pp 223-240.
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 595-606
    • Michael, J.P.1
  • 3
    • 0032413665 scopus 로고    scopus 로고
    • Ansell, M. F., Ed.; Elsevier: Amsterdam
    • For recent reviews, see (a) Michael, J. P. Nat. Prod. Rep. 1998, 15, 595-606. (b) Johne, S. In Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd edition); Ansell, M. F., Ed.; Elsevier: Amsterdam, 1995; Vol. IV I/J, pp 223-240.
    • (1995) Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd Edition) , vol.4 I-J , pp. 223-240
    • Johne, S.1
  • 9
    • 0345623795 scopus 로고    scopus 로고
    • Communication
    • (a) Communication: Wang, H.; Ganesan, A. J. Org. Chem. 1998, 63, 2432-2433.
    • (1998) J. Org. Chem. , vol.63 , pp. 2432-2433
    • Wang, H.1    Ganesan, A.2
  • 10
  • 13
    • 0343302077 scopus 로고    scopus 로고
    • note
    • In our initial studies, we used the cheaper L-amino acids, leading to the total synthesis of ent-fumiquinazoline G, which is summarized in the Experimental Section.
  • 16
    • 0343737607 scopus 로고    scopus 로고
    • note
    • Alternatively, tryptophan methyl ester was refluxed with isatoic anhydride in 1,2-dichloroethane to give 8 in 93% yield.
  • 18
    • 0018611071 scopus 로고
    • For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969- 4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 5084-5086
    • Büchi, G.1    DeShong, P.R.2    Katsumura, S.3    Sugimura, Y.4
  • 19
    • 0008204719 scopus 로고
    • For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969-4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4969-4972
    • Ohnuma, T.1    Kimura, Y.2    Ban, Y.3
  • 20
    • 0021060317 scopus 로고
    • For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969- 4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3709-3710
    • Nakagawa, M.1    Taniguchi, M.2    Sodeoka, M.3    Ito, M.4    Yamaguchi, K.5    Hino, T.6
  • 21
    • 0342866986 scopus 로고    scopus 로고
    • note
    • He and Snider (ref 8) were unsuccessful with such reactions on a similar peptide, although details are not given.
  • 23
    • 0342866982 scopus 로고    scopus 로고
    • note
    • We did not observe any enantiomer by NMR analysis with chiral lanthanide shift reagents (detection limit of 2% from control experiments).
  • 29
    • 0343302058 scopus 로고    scopus 로고
    • note
    • Although we use a neutral solvent, it is possible that the reaction is catalyzed by the piperidine byproduct released.
  • 30
    • 0343302059 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the natural product was not assigned, and we were unable to obtain a sample.
  • 31
    • 0343737590 scopus 로고    scopus 로고
    • note
    • For both fumiquinazoline F and fiscalin B, the melting point and optical rotation for our synthetic material is significantly higher than reported for the natural product, probably reflecting the difficulty of purifying the limited amount isolated and obtaining accurate measurements.
  • 32
    • 0342432509 scopus 로고    scopus 로고
    • note
    • 2.
  • 34
    • 0032481011 scopus 로고    scopus 로고
    • For our successful synthesis of luotonin A by another approach, see: Wang, H.; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097-9098.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9097-9098
    • Wang, H.1    Ganesan, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.