Synthesis of enantiomerically pure 3-aminochroman derivatives

被引：12
|
作者：
Usse, S
Pave, G
Guillaumet, G
Viaud-Massuard, MC
机构：
[1] Univ Orleans, UMR CNRS 6005, Inst Chim Organ & Anal, F-45067 Orleans 2, France
[2] UFR Sci Pharmaceut, Chim Organ Lab, F-37200 Tours, France
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 12期
关键词：
D O I：
10.1016/S0957-4166(01)00202-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Enantiomerically pure (3R)-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran was successfully synthesised in nine steps starting from L-serine. The same synthetic pathway was used to prepare the (3 S) -aminochroman derivative starting from D-serine. The enantiomeric purity of the final aminochroman derivatives was determined by capillary electrophoresis using P-cyclodextrin as the chiral selector. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1689 / 1694
页数：6
相关论文
共 50 条
  • [11] PRACTICAL SYNTHESIS OF ENANTIOMERICALLY PURE MYOINOSITOL DERIVATIVES
    BRUZIK, KS
    MYERS, J
    TSAI, MD
    TETRAHEDRON LETTERS, 1992, 33 (08) : 1009 - 1012
  • [12] Enantiomerically pure cyclobutane derivatives and their use in organic synthesis
    Lee-Ruff, E
    Mladenova, G
    CHEMICAL REVIEWS, 2003, 103 (04) : 1449 - 1483
  • [13] SYNTHESIS OF ENANTIOMERICALLY PURE PHOSPHONIC ANALOGS OF HOMOSERINE DERIVATIVES
    OUAZZANI, F
    ROUMESTANT, ML
    VIALLEFONT, P
    ELHALLAOUI, A
    TETRAHEDRON-ASYMMETRY, 1991, 2 (09) : 913 - 917
  • [14] Synthesis and biological evaluation of novel compounds within a class of 3-aminochroman derivatives with dual 5-HT1A receptor and serotonin transporter affinity
    Hatzenbuhler, Nicole T.
    Evrard, Deborah A.
    Harrison, Boyd L.
    Huryn, Donna
    Inghrim, Jennifer
    Kraml, Christina
    Mattes, James F.
    Mewshaw, Richard E.
    Zhou, Dahui
    Hornby, Geoffrey
    Lin, Qian
    Smith, Deborah L.
    Sullivan, Kelly M.
    Schechter, Lee E.
    Beyer, Chad E.
    Andree, Terrance H.
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) : 4785 - 4789
  • [15] Novel 2-aminotetralin and 3-AminoChroman derivatives as selective serotonin 5-HT7 receptor agonists and antagonists
    Holmberg, P
    Sohn, D
    Leideborg, R
    Caldirola, P
    Zlatoidsky, P
    Hanson, S
    Mohell, N
    Rosqvist, S
    Nordvall, G
    Johansson, AM
    Johansson, R
    JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (16) : 3927 - 3930
  • [16] THE SYNTHESIS AND BIOCHEMICAL PHARMACOLOGY OF ENANTIOMERICALLY PURE METHYLATED OXOTREMORINE DERIVATIVES
    TRYBULSKI, EJ
    ZHANG, J
    KRAMSS, RH
    MANGANO, RM
    JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) : 3533 - 3541
  • [17] Progress on the Synthesis of Enantiomerically Pure 3,4-Dihydropyrimidin-2-one Derivatives
    Rao, Honghong
    Quan, Zhengjun
    Bai, Lin
    Ye, Helin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) : 283 - 296
  • [18] SYNTHESIS OF ENANTIOMERICALLY PURE FLUOROCYCLOHEXANE AND GEM-CHLOROFLUOROCYCLOHEXANE DERIVATIVES
    ARNONE, A
    BRAVO, P
    FRIGERIO, M
    VIANI, F
    CAVICCHIO, G
    CRUCIANELLI, M
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21): : 6448 - 6455
  • [19] SYNTHESIS AND STRUCTURE OF ENANTIOMERICALLY PURE FERROCENE DERIVATIVES FOR NONLINEAR OPTICS
    TOGNI, A
    RIHS, G
    ORGANOMETALLICS, 1993, 12 (08) : 3368 - 3372
  • [20] Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives
    Kunig, Johannes
    Loennecke, Peter
    Hey-Hawkins, Evamarie
    CARBOHYDRATE RESEARCH, 2011, 346 (09) : 1154 - 1160
12345