Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation

被引:94
作者
Liu, JF [1 ]
Ye, P [1 ]
Zhang, BL [1 ]
Bi, G [1 ]
Sargent, K [1 ]
Yu, LB [1 ]
Yohannes, D [1 ]
Baldino, CM [1 ]
机构
[1] ArQule Inc, Div Chem Technol, Woburn, MA 01801 USA
关键词
D O I
10.1021/jo0508043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.
引用
收藏
页码:6339 / 6345
页数:7
相关论文
共 47 条
  • [1] Pd-assisted multicomponent synthesis of heterocycles
    Balme, G
    Bossharth, E
    Monteiro, N
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) : 4101 - 4111
  • [2] Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin
    Baran, PS
    O'Malley, DP
    Zografos, AL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) : 2674 - 2677
  • [3] Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
  • [4] 2-A
  • [5] Reactivity as glycine templates of 1,2-dialkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones
    Buenadicha, FL
    Avendaño, C
    Söllhuber, M
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (21) : 3019 - 3028
  • [6] Total synthesis of (±)-alantrypinone by hetero Diels-Alder reaction
    Chen, ZC
    Fan, JF
    Kende, AS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) : 79 - 85
  • [7] A new route toward 4-substituted pyrazino[2,1-b] qiuinazoline-3,6-dione systems.: Total synthesis of glyantrypine
    Cledera, P
    Avendaño, C
    Menéndez, JC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) : 1743 - 1749
  • [8] Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents
    Depew, KM
    Marsden, SP
    Zatorska, D
    Zatorski, A
    Bornmann, WG
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) : 11953 - 11963
  • [9] Recent advances in isocyanide-based multicomponent chemistry
    Dömling, A
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) : 306 - 313
  • [10] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO