Synthesis and X-ray structure of functionalised proline mimics

被引：0
作者：
Gardiner, J [1 ]
Abell, A [1 ]
机构：
[1] Univ Canterbury, Dept Chem, Private Bag 4800, Christchurch 1, New Zealand
来源：
ARKIVOC | 2004年
关键词：
proline mimetic; crystal structure; lactone; diol; dibromide;
D O I：
10.3998/ark.5550190.0005.a06
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Methyl (2R)-(1-benzoyl-2-benzyl-1,2,3,6-tetrahydropyridin-2-yl)carboxylate 1 reacts with osmium tetroxide to give two isomeric syn diols 2a and 2b and also with Br-2 to give two isomeric anti dibromides 4a and 4b. The major dibromide 4a gave rise to the lactone 5 on standing, the crystal structure of which is reported.
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页码：46 / 52
页数：7
相关论文
共 18 条
  • [1] Heterocyclic-based peptidomimetics
    Abell, AD
    [J]. LETTERS IN PEPTIDE SCIENCE, 2001, 8 (3-5): : 267 - 272
  • [2] Synthesis of substituted cyclohexenyl-based β-amino acids by ring-closing metathesis
    Abell, AD
    Gardiner, J
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3663 - 3666
  • [3] Ring-deactivated hydroxymethylpyrroles as inhibitors of α-chymotrypsin
    Abell, AD
    Nabbs, BK
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) : 621 - 628
  • [4] Synthesis and x-ray structure of a 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic
    Abell, AD
    Gardiner, J
    Phillips, AJ
    Robinson, WT
    [J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9563 - 9566
  • [5] Etzkorn FA, 1999, ADV AMIN AC MIM PEPT, V2, P125, DOI 10.1016/S1874-5113(99)80006-9
  • [6] GARDINER J, 2004, IN PRESS J ORG CHEM
  • [7] Code for collagen's stability deciphered
    Holmgren, SK
    Taylor, KM
    Bretscher, LE
    Raines, RT
    [J]. NATURE, 1998, 392 (6677) : 666 - 667
  • [8] Insights on the conformational stability of collagen
    Jenkins, CL
    Raines, RT
    [J]. NATURAL PRODUCT REPORTS, 2002, 19 (01) : 49 - 59
  • [9] Tetrazole analogues of cyclolinopeptide A: Synthesis, conformation, and biology
    Kaczmarek, K
    Jankowski, S
    Siemion, IZ
    Wieczorek, Z
    Benedetti, E
    Di Lello, P
    Isernia, C
    Saviano, M
    Zabrocki, J
    [J]. BIOPOLYMERS, 2002, 63 (06) : 343 - 357
  • [10] KOEP S, 2003, TETRAHEDRON LETT, V44, P1413
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