Pigments of Fungi. LXIII. Synthesis of (1S,3R)- and (1R,3S)-Austrocortilutein and the Enantiomeric Purity of Austrocortilutein in some Australian Dermocybe Toadstools

2000 ◽  
Vol 53 (1) ◽  
pp. 41 ◽  
Author(s):  
Catherine Elsworth ◽  
Melvyn Gill ◽  
Evelin Raudies ◽  
Abilio Ten
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity ◽  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Naturally Occurring ◽  
First Time

The naturally occurring tetrahydroanthraquinones (1S,3R)- and (1R,3S)-austrocortilutein (1b) and (1d), respectively, are synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (4) and the corresponding monochiral trans-1,3-dihydroxy-1,2,3,4- tetrahydro-5,8-naphthoquinone (5a) or (5b), themselves derived from citramalic acid. Separation of the four stereoisomeric austrocortiluteins by using h.p.l.c. over a chiral stationary phase reveals that the enantiomeric purity of the (1S,3S)- and (1R,3R)-quinones (1a) and (1c) varies from species to species whereas the (1S,3R)-isomer (1b) is, in the five cases examined, enantiomerically pure.

Pigments of Fungi. LIX. Synthesis of (1S,3S)- and (1R,3R)-Austrocortilutein and (1S,3S)-Austrocortirubin from Citramalic Acid

2000 ◽  
Vol 53 (4) ◽  
pp. 245 ◽  
Author(s):  
Melvyn Gill ◽  
Michael F. Harte ◽  
Abilio Ten
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Naturally Occurring ◽  
First Time

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy.

Determination of Repertaxin Enantiomeric Purity by HPLC on Chiral Stationary Phase

2015 ◽  
Vol 78 (23-24) ◽  
pp. 1485-1489 ◽  
Author(s):  
Yongmei Liu ◽  
Mengya Liao ◽  
Cuiwei Zhang ◽  
Yuli Bai ◽  
Honglian Song ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity

ChemInform Abstract: Asymmetric Diels-Alder Reactions of Chiral (E)-2-Cyanocinnamates. Part 2. Synthesis of the Four 1-Amino-2-phenyl-1-cyclohexanecarboxylic Acids in Enantiomerically Pure Form.

ChemInform ◽  
2010 ◽  
Vol 26 (25) ◽  
pp. no-no
Author(s):  
C. CATIVIELA ◽  
A. AVENOZA ◽  
M. PARIS ◽  
J. M. PEREGRINA
Keyword(s):  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure

Determination of the enantiomeric purity of (??) 2-(N-propyl-n-2-thienylethylamino)-5-hydroxytetralin (n-0923) by chiral stationary phase HPLC

Chirality ◽  
1992 ◽  
Vol 4 (1) ◽  
pp. 62-64 ◽  
Author(s):  
Dirk T. Witte ◽  
Jan-Piet Franke ◽  
Pieter J. Swart ◽  
Rokus A. De Zeeuw
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity

Determination of Roscovitine Enantiomeric Purity by HPLC on Chiral Stationary Phase

2016 ◽  
Vol 79 (9-10) ◽  
pp. 641-646 ◽  
Author(s):  
Guangjie Xie ◽  
Mengya Liao ◽  
Bangyu Wang ◽  
Cuiwei Zhang
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity

Determination of Enantiomeric Purity of GSK962040 Based on Liquid Chromatography Using Chiral Stationary Phase Combined with a Pre-column Derivatization Procedure

2017 ◽  
Vol 80 (8) ◽  
pp. 1257-1262 ◽  
Author(s):  
Tinghong Ye ◽  
Mengya Liao ◽  
Mingxing Hu ◽  
Yongmei Xie ◽  
Yiwen Zhang
Keyword(s):  
Liquid Chromatography ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity

Asymmetric Diels-Alder Reactions of Chiral (E)-2-Cyanocinnamates. 2. Synthesis of the Four 1-Amino-2-phenyl-1-cyclohexanecarboxylic Acids in Enantiomerically Pure Form

1994 ◽  
Vol 59 (25) ◽  
pp. 7774-7778 ◽  
Author(s):  
Carlos Cativiela ◽  
Alberto Avenoza ◽  
Miguel Paris ◽  
Jesus M. Peregrina
Keyword(s):  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure

scholarly journals The First Liquid-Chromatographic Separation of the (R)- and (S)-Enantiomers of a Chiral Silanol, Silane and Germane

1995 ◽  
Vol 50 (4) ◽  
pp. 568-572 ◽  
Author(s):  
Reinhold Tacke ◽  
Dirk Reichel ◽  
Kurt Günther ◽  
Stefan Merget
Keyword(s):  
Chiral Stationary Phase ◽  
Enantiomeric Purity ◽  
Nmr Studies ◽  
Enantiomerically Pure ◽  
Chemically Modified ◽  
Liquid Chromatographic Separation ◽  
Racemic Mixtures ◽  
Liquid Chromatographic ◽  
C Nmr

The racemic mixtures of the muscarinic antagonists cyclohexyl(phenyl)(2-pyrrolidinoethyl)silanol (sila-procyclidine, rac-1), cyclohexyl(hydroxymethyl)phenyl(2-piperidinoethyl)-silane (rac-2) and cyclohexyl(hydroxymethyl)phenyl(2-piperidinoethyl)germane (rac-3) were resolved by analytical liquid chromatography (HPLC) using chemically modified cellulose (1) or amylose (2, 3) as the chiral stationary phase. This chromatographic method was used for the quantitative determination of enantiomeric purity of the (R)- and (S)-enantiomers of 1 - 3 , which were obtained by preparative resolution with chiral auxiliary agents. Furthermore, the enantiomeric purity of these samples was established by 13C NMR studies using chiral shift reagents. According to these studies, the resolved antipodes of 1 - 3 (obtained by preparative resolution) were almost enantiomerically pure [HPLC: ≥ 98.2% ee ((R )-3) to 99.4% ee ((R)-1, (S)-1); NMR: ≥ 97% ee].

Enantiomeric Separation of 1-Phenyl-1-Propanol Using Calix[4]Arene-Capped β-Cyclodextrin-Bonded Silica Particles as Chiral Stationary Phase in Capillary Electrochromatography

2013 ◽  
Vol 749 ◽  
pp. 304-308 ◽  
Author(s):  
Jia Zhao ◽  
Jun Li ◽  
E.L. Yong ◽  
Yin Han Gong
Keyword(s):  
Stationary Phase ◽  
Capillary Electrochromatography ◽  
Chiral Stationary Phase ◽  
Enantiomeric Separation ◽  
Silica Particles ◽  
Hydroxyl Groups ◽  
New Type ◽  
Phenolic Hydroxyl Groups ◽  
First Time ◽  
Calix Arene

A new type of calix [ arene-capped (3-(2-O-β-cyclodextrin)-2-hydroxypropoxy) propylsilyl-appended silica particles (C4CD-HPS) has been successfully used as chiral stationary phase (CSP) in capillary electrochromatography (CEC) for separation of enantiomers of 1-phenyl-1-propanol for the first time. C4CD-HPS contains a chiral selector with two recognition sites: calix [arene and β-cyclodextrin. Due to the cooperative functioning of the calix [arene and β-cyclodextrin, C4CD-HPS has exhibited excellent enantioselectivity for the enantiomers of 1-phenyl-1-propanol. After the multiple phenolic hydroxyl groups in the calix [arene moieties are ionized in the running buffer, the bonded stationary phase C4CD-HPS becomes negatively-charged to provide high electroosmotic flow (EOF) in CEC. Fast and high-resolution separation for enantiomers of 1-phenyl-1-propanol has been easily achieved on C4CD-HPS. This new type of chiral stationary phase has exhibited great potential for fast enantiomeric separations in CEC.

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