Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin

被引:101
作者
Baran, PS [1 ]
O'Malley, DP [1 ]
Zografos, AL [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
D O I
10.1002/anie.200453937
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Microwave-induced magic: There is a widely held conviction that the antiviral marine alkaloid ageliferin 1 arises biosynthetically from a Diels-Alder reaction which, although possible, has yet to materialize in the laboratory. A total synthesis of 1 from sceptrin is now reported that has led to a new hypothesis for how 1 and other dimeric pyrrole-imidazole alkaloids might be formed in nature.
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页码:2674 / 2677
页数:4
相关论文
共 25 条
  • [1] Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
  • [2] Assmann M, 2002, Z NATURFORSCH C, V57, P157
  • [3] ASSMANN M, COMMUNICATION
  • [4] ASSMANN M, 2004, IN PRESS P 6 INT SPO
  • [5] Short total synthesis of (±)-sceptrin
    Baran, PS
    Zografos, AL
    O'Malley, DP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3726 - 3727
  • [6] Photochemical dimerization of esters of urocanic acid
    D'Auria, M
    Racioppi, R
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1998, 112 (2-3) : 145 - 148
  • [7] FLEMING I, 1999, PERICYCLIC REACTIONS, P75
  • [8] Intramolecular Diels-Alder reactions of 4-vinylimidazoles
    He, Y
    Chen, YZ
    Wu, HY
    Lovely, CJ
    [J]. ORGANIC LETTERS, 2003, 5 (20) : 3623 - 3626
  • [9] Synthesis of the pyrrole-imidazole alkaloids
    Hoffmann, H
    Lindel, T
    [J]. SYNTHESIS-STUTTGART, 2003, (12): : 1753 - 1783
  • [10] Novel Diels-Alder-type dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to biomimetic synthesis of 12,12′-dimethylageliferin
    Kawasaki, I
    Sakaguchi, N
    Fukushima, N
    Fujioka, N
    Nikaido, F
    Yamashita, M
    Ohta, S
    [J]. TETRAHEDRON LETTERS, 2002, 43 (24) : 4377 - 4380