Synthesis of (-)-TAN1251A using 4-hydroxy-L-proline as a chiral source

被引:23
|
作者
Nagumo, S [1 ]
Matoba, A [1 ]
Ishii, Y [1 ]
Yamaguchi, S [1 ]
Akutsu, N [1 ]
Nishijima, H [1 ]
Nishida, A [1 ]
Kawahara, N [1 ]
机构
[1] Hokkaido Coll Pharm, Otaru, Hokkaido 0470264, Japan
关键词
(-)-TAN1251A; anti-muscarinic activity; synthesis 1-azaspiro[4.5]decane; trans-4-hydroxy-L-proline;
D O I
10.1016/S0040-4020(02)01292-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthetic route of (-)-TAN1251A possessing an antimuscarinic activity was developed on the basis of alkylation of a trans-4-hydroxy-L-proline derivative and the subsequent construction of an azaspiro ring as key steps. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:9871 / 9877
页数:7
相关论文
共 50 条
  • [41] STUDIES OF BLADDER STONE DISEASE IN THAILAND .16. EFFECT OF 4-HYDROXY-L-PROLINE AND ORTHOPHOSPHATE SUPPLEMENTATIONS ON URINARY COMPOSITION AND CRYSTALLURIA
    VALYASEVI, A
    DHANAMITTA, S
    VANREEN, R
    AMERICAN JOURNAL OF CLINICAL NUTRITION, 1973, 26 (11): : 1207 - 1211
  • [42] Nuclear magnetic resonance studies of thyrotropin-releasing hormone (TRH) and analogues incorporating D-histidine and 4-hydroxy-L-proline
    Aksnes, DW
    Athanassopoulos, C
    Magafa, V
    Aaberg, A
    Francis, GW
    Papaioannou, D
    ACTA CHEMICA SCANDINAVICA, 1996, 50 (05): : 411 - 416
  • [43] ISOLATION AND SYNTHESIS OF 3-HYDROXY-L-PROLINE
    IRREVERRE, F
    WITKOP, B
    ROBERTSON, AV
    MORITA, K
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1962, 8 (06) : 453 - &
  • [44] Synthesis and characterization of degradable copoly(trans-4-hydroxy-L-proline/ε-caprolactone)
    Lee, RS
    Yang, JM
    JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 88 (14) : 3176 - 3182
  • [45] Stereocontrolled synthesis of (-)-kainic acid from trans-4-hydroxy-L-proline
    Poisson, JF
    Orellana, A
    Greene, AE
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26): : 10860 - 10863
  • [46] Synthesis and characterization of degradable copoly(trans-4-hydroxy-L-proline/Ε-caprolactone)
    Lee, Ren-Shen
    Yang, Jen-Ming
    1600, John Wiley and Sons Inc. (88):
  • [47] Synthesis of a constrained tricyclic scaffold based on trans-4-hydroxy-L-proline
    Trabocchi, A
    Rolla, M
    Menchi, G
    Guarna, A
    TETRAHEDRON LETTERS, 2005, 46 (45) : 7813 - 7816
  • [48] An efficient procedure for the production of trans-4-hydroxy-L-proline using recombinantly expressed proline hydroxylase
    Chen, J. J.
    Gu, D. D.
    Li, T. Y.
    Ju, J. S.
    Xue, Zh. W.
    Li, C. H.
    Yan, J.
    Zhang, J. X.
    Wang, L. A.
    SCIENTIA IRANICA, 2015, 22 (06) : 2350 - 2357
  • [49] Enzymatic production oftrans-4-hydroxy-l-proline by proline 4-hydroxylase
    Chen, Xiulai
    Yi, Juyang
    Liu, Jia
    Luo, Qiuling
    Liu, Liming
    MICROBIAL BIOTECHNOLOGY, 2021, 14 (02): : 479 - 487
  • [50] NOVEL N,N'-METHYLENE-BRIDGED METAL(II) COMPLEXES OF N,N'-METHYLENEDI(4-HYDROXY-L-PROLINE) OBTAINED FROM THE CONDENSATION OF BIS(4-HYDROXY-L-PROLINATO)METAL(II) WITH FORMALDEHYDE
    TEO, SB
    TEOH, SG
    NG, CH
    FUN, HK
    DECLERCQ, JP
    POLYHEDRON, 1995, 14 (11) : 1447 - 1451