Synthesis of cyclic dipeptides by ring-closing metathesis

被引：0
|
作者：
Reichwein, JF [1 ]
Liskamp, RMJ [1 ]
机构：
[1] Univ Utrecht, Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 12期
关键词：
ring closure; metathesis; peptides; peptidomimetics; cyclization; dienes;
D O I：
10.1002/1099-0690(200006)2000:12<2335::AID-EJOC2335>3.0.CO;2-C
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.
引用
收藏
页码：2335 / 2344
页数：10
相关论文
共 50 条
  • [1] Synthesis of cyclic peptides by ring-closing metathesis
    Reichwein, JF
    Versluis, C
    Liskamp, RMJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 6187 - 6195
  • [2] Synthesis of cyclic peptidosulfonamides by ring-closing metathesis
    Brouwer, AJ
    Liskamp, RMJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11): : 3662 - 3668
  • [3] Synthesis of cyclic sulfones by ring-closing metathesis
    Yao, QW
    [J]. ORGANIC LETTERS, 2002, 4 (03) : 427 - 430
  • [4] Synthesis of cyclic enehydrazides by ring-closing metathesis
    Lebrun, Stephane
    Couture, Axel
    Deniau, Eric
    Grandclaudon, Pierre
    [J]. SYNTHESIS-STUTTGART, 2006, (20): : 3490 - 3494
  • [5] Ring-closing metathesis in the synthesis of cyclic α-amino acids
    Osipov, SN
    Dixneuf, P
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (09) : 1211 - 1220
  • [6] Ring-closing metathesis (RCM) for the synthesis of cyclic sulfoximines
    Bolm, C
    Villar, H
    [J]. SYNTHESIS-STUTTGART, 2005, (09): : 1421 - 1424
  • [7] Ring-Closing Metathesis in the Synthesis of Cyclic α-Amino Acids
    S. N. Osipov
    P. Dixneuf
    [J]. Russian Journal of Organic Chemistry, 2003, 39 : 1211 - 1220
  • [8] Synthesis of cyano cyclic olefins through ring-closing metathesis
    Choi, IY
    Byoun, KH
    Jung, MH
    Lim, HJ
    Lee, HW
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (09): : 1305 - 1306
  • [9] Ring-Closing Enyne Metathesis (RCEYM) for the Synthesis of Cyclic Sulfoximines
    Fueger, Bernhard
    Bolm, Carsten
    [J]. SYNLETT, 2009, (10) : 1601 - 1604
  • [10] Novel synthesis of cyclic alkenylboronates via ring-closing metathesis
    Renaud, J
    Ouellet, SG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (31) : 7995 - 7996
12345