Efficient synthesis and resolution of pyrrolizidines

被引:43
作者
de Figueiredo, Renata Marcia
Froehlich, Roland
Christmann, Mathias
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
antitumor agents; chiral resolution; lactonization; natural products; organocatalysis;
D O I
10.1002/anie.200605035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In only two steps the commercially available maleimide 1 is converted into the key pyrrolizidine carboxylic acid unit (2) of the telomerase inhibitor UCS1025A. A kinetic resolution through an enantioselective oxa-Michael lactonization and trituration of the resulting scalemic mixture allow for a virtually quantitative separation of a racemate into the enantiomers. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2883 / 2886
页数:4
相关论文
共 18 条
  • [1] UCS1025A and B, new antitumor antibiotics from the fungus Acremonium species
    Agatsuma, T
    Akama, T
    Nara, S
    Matsumiya, S
    Nakai, R
    Ogawa, H
    Otaki, S
    Ikeda, S
    Saitoh, Y
    Kanda, Y
    [J]. ORGANIC LETTERS, 2002, 4 (25) : 4387 - 4390
  • [2] Synthesis of a malimide analogue of the telomerase inhibitor UCS1025A using a dianionic aldol strategy
    de Figueiredo, Renata Marcia
    Voith, Matthias
    Froehlich, Roland
    Christmann, Mathias
    [J]. SYNLETT, 2007, (03) : 391 - 394
  • [3] Hayashi Y., 2006, ANGEW CHEM, V28, P4709
  • [4] Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state
    Hayashi, Yujiro
    Matsuzawa, Masayoshi
    Yamaguchi, Junichiro
    Yonehara, Sayaka
    Matsumoto, Yasunobu
    Shoji, Mitsuru
    Hashizume, Daisuke
    Koshino, Hiroyuki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) : 4593 - 4597
  • [5] ADDITION OF AROMATIC THIOLS TO CONJUGATED CYCLOALKENONES, CATALYZED BY CHIRAL BETA-HYDROXY AMINES - A MECHANISTIC STUDY ON HOMOGENEOUS CATALYTIC ASYMMETRIC-SYNTHESIS
    HIEMSTRA, H
    WYNBERG, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) : 417 - 430
  • [6] Silylative Dieckmann-like cyclizations of ester-imides (and diesters)
    Hoye, Thomas R.
    Dvornikovs, Vadims
    Sizova, Elena
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5191 - 5194
  • [7] Comparative Diels-Alder reactivities within a family of valence bond isomers:: A biomimetic total synthesis of (±)-UCS1025A
    Hoye, TR
    Dvornikovs, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2550 - 2551
  • [8] Thermodynamic control of asymmetric amplification in amino acid catalysis
    Klussmann, Martin
    Iwamura, Hiroshi
    Mathew, Suju P.
    Wells, David H., Jr.
    Pandya, Urvish
    Armstrong, Alan
    Blackmond, Donna G.
    [J]. NATURE, 2006, 441 (7093) : 621 - 623
  • [9] Krause N, 2001, SYNTHESIS-STUTTGART, P171
  • [10] Total synthesis of UCS1025A
    Lambert, TH
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 426 - 427