Synthesis of the C-1027 chromophore framework through atropselective macrolactonization

被引：34
作者：
Inoue, M [1 ]
Sasaki, T
Hatano, S
Hirama, M
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 47期
关键词：
alkynes; antitumor agents; atropisomerism; lactones; macrocycles;
D O I：
10.1002/anie.200461428
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Long-range steric interactions of the protecting groups of the 1,5-diol were harnessed for the successful atropselective macrolactonization (A) in the synthesis of the C-1027 chromophore framework (see scheme). Subsequent LiN(SiMe3)2/CeCl3-promoted acetylide addition to an aldehyde (B) in the setting of a rigid macrocycle formed the target nine-membered ring system with a highly strained diyne. (Chemical equation presented).
引用
收藏
页码：6500 / 6505
页数：6
相关论文
共 60 条
  • [1] Total synthesis of the vancomycin aglycon
    Boger, DL
    Miyazaki, S
    Kim, SH
    Wu, JH
    Castle, SL
    Loiseleur, O
    Jin, Q
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) : 10004 - 10011
  • [2] Studies toward the synthesis of natural and unnatural dienediynes 1. Approaches to a functionalised bicyclic ring system
    Caddick, S
    Delisser, VM
    Doyle, VE
    Khan, S
    Avent, AG
    Vile, S
    [J]. TETRAHEDRON, 1999, 55 (09) : 2737 - 2754
  • [3] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES
    COREY, EJ
    NICOLAOU, KC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) : 5614 - 5616
  • [4] Observations in the chemistry and biology of cyclic enediyne antibiotics: Total syntheses of calicheamicin gamma(I)(1) and dynemicin A
    Danishefsky, SJ
    Shair, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 16 - 44
  • [5] DOI T, 1991, J ORG CHEM, V56, P3465, DOI 10.1021/jo00011a002
  • [6] Evans D. A., 1998, ANGEW CHEM, V110, P2868
  • [7] Evans D.A., 1998, ANGEW CHEM, V110, P2864
  • [8] Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2704, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO
  • [9] 2-1
  • [10] Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2700, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO
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