Synthesis and the absolute configuration of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis

2015 ◽  
Vol 13 (3) ◽  
pp. 807-816 ◽  
Author(s):  
Beata Łukasik ◽  
Marian Mikołajczyk ◽  
Grzegorz Bujacz ◽  
Remigiusz Żurawiński
Keyword(s):  
Tartaric Acid ◽  
Absolute Configuration ◽  
Building Block ◽  
Chiral Building Block ◽  
The Absolute ◽  
Prostanoid Synthesis

Starting from optically inactive meso-tartaric acid (6) the synthesis of both enantiomers of a new cyclopentenone building block 5 was developed.

Synthesis of the antipode of udoteatrial hydrate using (+)-genipin as a chiral building block: Determination of the absolute configuration of udoteatrial hydrate

1993 ◽  
Vol 34 (16) ◽  
pp. 2621-2624 ◽  
Author(s):  
Yuting Ge ◽  
Shoichi Kondo ◽  
Yoshihiko Odagaki ◽  
Shigeo Katsumura ◽  
Kazuhiko Nakatani ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Building Block ◽  
Chiral Building Block ◽  
The Absolute

On the Absolute Configuration of (+)-Tartaric Acid

1985 ◽  
Vol 24 (6) ◽  
pp. 513-513 ◽  
Author(s):  
Hartmuth Buding ◽  
Bertold Deppisch ◽  
Hans Musso ◽  
G�nther Snatzke
Keyword(s):  
Tartaric Acid ◽  
Absolute Configuration ◽  
The Absolute

D3-Trishomocubane-4-carboxylic Acid as a New Chiral Building Block: Synthesis and Absolute Configuration

Synthesis ◽  
2012 ◽  
Vol 44 (05) ◽  
pp. 810-816 ◽  
Author(s):  
Dmitriy Volochnyuk ◽  
Igor Levandovskiy ◽  
Tatyana Shubina ◽  
Alexandr Gaidai ◽  
Oleg Shishkin ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Building Block ◽  
Chiral Building Block

Evaluation of Different Synthetic Routes to (2R,3R)-3-Hydroxymethyl-2-(4-hydroxy- 3-methoxyphenyl)-1,4-Benzodioxane-6-Carbaldehyde

2020 ◽  
Vol 23 (26) ◽  
pp. 2960-2968
Author(s):  
Renáta Kertiné Ferenczi ◽  
Tünde-Zita Illyés ◽  
Sándor Balázs Király ◽  
Gyula Hoffka ◽  
László Szilágyi ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Stereoselective Synthesis ◽  
Cotton Effect ◽  
Enantioselective Synthesis ◽  
Aryl Group ◽  
Target Molecule ◽  
Synthetic Routes ◽  
The Absolute

The reported enantioselective synthesis for the preparation of (+)-(2R,3R)-2-(4- hydroxy-3-methoxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-carbaldehyde, precursor for the stereoselective synthesis of bioactive flavanolignans, could not be reproduced. Thus, the target molecule was prepared via the synthesis and separation of diastereomeric O-glucosides. TDDFT-ECD calculations and the 1,4-benzodioxane helicity rule were utilized to determine the absolute configuration. ECD calculations also confirmed that the 1Lb Cotton effect is governed by the helicity of the heteroring, while the higher-energy ECD transitions reflect mainly the orientation of the equatorial C-2 aryl group.

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