An efficient synthesis of enantiomerically pure (1R,2S,5S)- and (1S,2R,5R)-rosaprostol methyl esters

被引：6
|
作者：
Murcia, M. Carmen [1 ]
de la Herran, Gabriela [1 ]
Plumet, Joaquin [1 ]
Csaky, Aurelio G. [1 ]
机构：
[1] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain
来源：
SYNLETT | 2007年 / 10期
关键词：
cyclopentenones; Grignard reactions; Michael additions; stereoselective synthesis; prostanoids;
D O I：
10.1055/s-2007-982558
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a concise synthesis of the enantiomerically pure 1,2-trans-1,5-cis-methyl esters of rosaprostol, a prostaglandin derivative used for the treatment of gastric and duodenal ulcers, using as key step the chemo- and stereoselective Michael addition of a Grignard reagent to an unprotected hydroxycyclopentenone.
引用
收藏
页码：1553 / 1556
页数：4
相关论文
共 50 条
  • [1] Catalytic hydroformylation of (1S,5S)-(-)- and (1R,5R)-(+)-beta-pinene: Stereoselective synthesis and spectroscopic characterization of (1S,2R,5S)-, (1S,2S,5S)-, (1R,2R,5R)- and (1R,2S,5R)-10-formylpinane
    Azzaroni, F
    Biscarini, P
    Bordoni, S
    Longoni, G
    Venturini, E
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 508 (1-2) : 59 - 67
  • [2] Substituent Effect on the Asymmetric Induction with (1R,2S,5R)-and (1S,2R,5S)-menthol Auxiliaries
    Er, Mustafa
    Coskun, Necdet
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2010, 32 (02): : 198 - 208
  • [3] Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin
    Bravo, P
    Corradi, E
    Frigerio, M
    Meille, SV
    Panzeri, W
    Pesenti, C
    Viani, F
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6317 - 6320
  • [4] Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)and (1S,2R,5R)-5-methyl-cispentacin
    Abraham, Elin
    Davies, Stephen G.
    Docherty, Alexander J.
    Ling, Kenneth B.
    Roberts, Paul M.
    Russell, Angela J.
    Thomson, James E.
    Toms, Steven M.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (11) : 1356 - 1362
  • [5] Efficient synthesis of (1R,2S) and (1S,2R)-2-aminocyclopentanecarboxylic acid ethyl ester derivatives in enantiomerically pure form
    Dragovich, Peter S.
    Murphy, Douglas E.
    Dao, Kimkim
    Kim, Sun Hee
    Li, Lian-Sheng
    Ruebsam, Frank
    Sun, Zhongxiang
    Tran, Chinh V.
    Xiang, Alan X.
    Zhou, Yuefen
    TETRAHEDRON-ASYMMETRY, 2008, 19 (24) : 2796 - 2803
  • [6] Synthesis of enantiomerically pure (1R,2R)- and (1S,2S)-2-alkyl-1-phenylsulfonylcyclopropanes using Bakers' yeast
    Tanikaga, R
    Shibata, N
    Yoneda, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (15): : 2253 - 2257
  • [7] An efficient stereoselective synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine
    Chavan, SP
    Praveen, C
    Sharma, P
    Kalkote, UR
    TETRAHEDRON LETTERS, 2005, 46 (03) : 439 - 441
  • [8] Synthesis of enantiomerically pure (1R,2S)- and (1S,2R)-2-amino-1,2-bis(pentafluorophenyl)ethanols
    Sakai, T
    Kubo, K
    Kashino, S
    Uneyama, K
    TETRAHEDRON-ASYMMETRY, 1996, 7 (07) : 1883 - 1886
  • [9] ENZYMATIC PREPARATION OF ENANTIOMERICALLY PURE (1R,2R)-2-AMINOCYCLOHEXANOLS AND (1S,2S)-2-AMINOCYCLOHEXANOLS
    TAKADA, H
    TAKAGI, S
    KAWAKUBO, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (04) : 1196 - 1197
  • [10] SYNTHESIS OF ENANTIOMERICALLY PURE (1S,2R)-EPOXY INDANE AND CIS-(1R,2S)-2-AMINO-1-INDANOL
    MITROCHKINE, A
    EYDOUX, F
    MARTRES, M
    GIL, G
    HEUMANN, A
    REGLIER, M
    TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 59 - 62
12345