Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

被引:28
|
作者
Wang, Q [1 ]
Sasaki, NA [1 ]
Potier, P [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
peptidomimetics; chimeras; 4-substituted prolines; 2,4-disubstituted pyrrolidines;
D O I
10.1016/S0040-4020(98)00989-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of readily available chiral building block 1 with (2R)-2,3-O-isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline-glutamic acid, are synthesized in highly diastereomerically pure forms, (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:15759 / 15780
页数:22
相关论文
共 50 条
  • [1] SYNTHESIS OF 4-SUBSTITUTED PROLINES AS CONFORMATIONALLY CONSTRAINED AMINO-ACID ANALOGS
    KOSKINEN, AMP
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08): : 1859 - 1866
  • [2] SYNTHESIS OF CONFORMATIONALLY CONSTRAINED ANALOGUES OF BIOACTIVE AMINO ACIDS BASED ON ASYMMETRIC CYCLOPROPANATION
    Midura, Wanda H.
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (05) : 1189 - 1192
  • [3] Stereoselective synthesis of conformationally constrained ω-amino acid analogues from pyroglutamic acid
    Bentz, EL
    Goswami, R
    Moloney, MG
    Westawayb, SM
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (15) : 2872 - 2882
  • [4] An efficient method for the stereoselective synthesis of cis-3-substituted prolines:: conformationally constrained α-amino acids
    Flamant-Robin, C
    Wang, Q
    Chiaroni, A
    Sasaki, NA
    [J]. TETRAHEDRON, 2002, 58 (52) : 10475 - 10484
  • [5] Synthesis of conformationally constrained analogues of (R)-2-amino-7-phosphonoheptanoic acid
    Langlois, N
    RojasRousseau, A
    Decavallas, O
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 1095 - 1100
  • [6] Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide
    Yamada, Takeshi
    Okada, Takuya
    Sakaguchi, Kazuhiko
    Ohfune, Yasufumi
    Ueki, Hisanori
    Soloshonok, Vadim A.
    [J]. ORGANIC LETTERS, 2006, 8 (24) : 5625 - 5628
  • [7] CONFORMATIONALLY CONSTRAINED AMINO-ACIDS .2. ON THE SYNTHESIS OF 4-SUBSTITUTED 8-MEMBERED CYCLIC TRYPTOPHAN DERIVATIVES
    CHUNG, JYL
    WASICAK, JT
    NADZAN, AM
    [J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (07) : 1039 - 1048
  • [8] Constrained amino acids, an approach to the synthesis of 3-substituted prolines
    Waid, PP
    Flynn, GA
    Huber, EW
    Sabol, JS
    [J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4091 - 4094
  • [9] 4-Substituted prolines as organocatalysts for aldol reactions
    Bellis, E
    Kokotos, G
    [J]. TETRAHEDRON, 2005, 61 (36) : 8669 - 8676
  • [10] Synthesis of a conformationally constrained δ-amino acid building block
    Elaine O’Reilly
    Lara Pes
    Yannick Ortin
    Helge Müller-Bunz
    Francesca Paradisi
    [J]. Amino Acids, 2013, 44 : 511 - 518