A short-step synthesis of (2S,3R)-3-hydroxy-3-methylproline, a component of polyoxypeptins, using a tandem Michael-Aldol reaction and optical resolution

被引:8
作者
Makino, K [1 ]
Suzuki, T [1 ]
Hamada, Y [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
D O I
10.1246/bcsj.77.1649
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A short-step synthesis of (2S,3R)-3-hydroxy-3-inethylproline, a component of polyoxypeptins, using a tandem Michael-aldol reaction followed by its optical resolution using (-)-cinchonidine has been achieved.
引用
收藏
页码:1649 / 1653
页数:5
相关论文
共 19 条
  • [1] Lipase TL-mediated kinetic resolution of 5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at low temperature:: Concise asymmetric synthesis of both enantiomers of a piperazic acid derivative
    Aoyagi, Y
    Saitoh, Y
    Ueno, T
    Horiguchi, M
    Takeya, K
    Williams, RM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6899 - 6904
  • [2] AN IMPROVED SYNTHESIS OF PYRROLES FROM N-PARA-TOLUENESULFONYLGLYCINE ESTERS AND ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES
    LASH, TD
    HOEHNER, MC
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) : 1671 - 1676
  • [3] A practical synthesis of the lipophilic side chain of the polyoxypeptins
    Lorca, M
    Kurosu, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (13) : 2431 - 2434
  • [4] Synthesis of the acyl side chain segment of polyoxypeptins using regioselective ring-opening of chiral 2,3-epoxy alcohol
    Makino, K
    Suzuki, T
    Awane, S
    Hara, O
    Hamada, Y
    [J]. TETRAHEDRON LETTERS, 2002, 43 (51) : 9391 - 9395
  • [5] Synthetic studies on polyoxypeptins:: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline using SmI2-mediated cyclization
    Makino, K
    Kondoh, A
    Hamada, Y
    [J]. TETRAHEDRON LETTERS, 2002, 43 (26) : 4695 - 4698
  • [6] Makino K, 2002, SYNLETT, P613
  • [7] Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution
    Makino, K
    Okamoto, N
    Hara, O
    Hamada, Y
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (12) : 1757 - 1762
  • [8] Synthetic study of polyoxypeptin: stereoselective synthesis of the acyl side-chain segment
    Noguchi, Y
    Yamada, T
    Uchiro, H
    Kobayashi, S
    [J]. TETRAHEDRON LETTERS, 2000, 41 (39) : 7499 - 7502
  • [9] Synthetic study of polyoxypeptin:: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline
    Noguchi, Y
    Uchiro, H
    Yamada, T
    Kobayashi, S
    [J]. TETRAHEDRON LETTERS, 2001, 42 (31) : 5253 - 5256
  • [10] Diastereoselective synthesis of all stereoisomers of β-methoxytyrosine, a component of papuamides
    Okamoto, N
    Hara, O
    Makino, K
    Hamada, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) : 9210 - 9215