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
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
  • [21] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
    Vivek D. Bobade
    Pravin C. Mhaske
    Kamlesh S. Vadgaonkar
    Shivaji H. Shelke
    [J]. Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 847 - 851
  • [22] Synthesis of the mycolactone core by ring-closing metathesis
    Alexander, Matthew D.
    Fontaine, Shaun D.
    La Clair, James J.
    DiPasquale, Antonio G.
    Rheingold, Arnold L.
    Burkart, Michael D.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (44) : 4602 - 4604
  • [23] Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans
    Schmidt, B
    Wildemann, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18): : 5817 - 5822
  • [24] Synthesis of bicyclic nucleosides by ring-closing metathesis
    Ravn, J
    Nielsen, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09): : 985 - 993
  • [25] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
    Bobade, Vivek D.
    Mhaske, Pravin C.
    Vadgaonkar, Kamlesh S.
    Shelke, Shivaji H.
    [J]. MONATSHEFTE FUR CHEMIE, 2012, 143 (05): : 847 - 851
  • [26] Synthesis of Azaheterocyclic Vinylphosphonates by Ring-Closing Metathesis
    Garzon, Cecile
    Attolini, Mireille
    Maffei, Michel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (18) : 3653 - 3657
  • [27] Ring-closing metathesis for the synthesis of a molecular gyrotop
    Setaka, Wataru
    Higa, Sayaka
    Yamaguchi, Kentaro
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (21) : 3354 - 3357
  • [28] Synthesis of "glycospirostanes" via ring-closing metathesis
    Czajkowska, Dorota
    Morzycki, Jacek W.
    Santillan, Rosa
    Siergiejczyk, Leszek
    [J]. STEROIDS, 2009, 74 (13-14) : 1073 - 1079
  • [29] Synthesis of cyclitols via ring-closing metathesis
    Kornienko, A
    d'Alarcao, M
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (05) : 827 - 829
  • [30] Ring-closing metathesis in the synthesis of fused sultones
    Mondal, Shovan
    Debnath, Sudatshan
    [J]. TETRAHEDRON LETTERS, 2014, 55 (09) : 1577 - 1580