The absolute configuration of isochamigrene: new insights into the cyclisation mechanism of trichodiene synthase

2018 ◽  
Vol 54 (28) ◽  
pp. 3540-3542 ◽  
Author(s):  
Immo Burkhardt ◽  
Jeroen S. Dickschat
Keyword(s):  
Absolute Configuration ◽  
Enantioselective Synthesis ◽  
Trichodiene Synthase ◽  
The Absolute

The enantioselective synthesis of isochamigrene clarified its absolute configuration and biosynthetic relation to trichodiene.

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.

scholarly journals Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

2021 ◽  
Author(s):  
Eryn Nelson ◽  
Jeffrey S. S. K. Formen ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Rapid Determination ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Widespread Occurrence ◽  
Chiral Compounds ◽  
New Methods ◽  
The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

Enantioselective Synthesis and Photoreactivity of a Diazirinyl-substituted (R)-β-Phenylalanine

2014 ◽  
Vol 69 (11-12) ◽  
pp. 1088-1096 ◽  
Author(s):  
Jan-Niklas Schäckermann ◽  
Thomas Lindel
Keyword(s):  
Amino Acid ◽  
Absolute Configuration ◽  
Enantioselective Synthesis ◽  
Thermally Stable ◽  
Standard Laboratory ◽  
Laboratory Conditions ◽  
Quantumchemical Calculations ◽  
Valence Tautomers ◽  
The Absolute

Abstract The first enantioselective synthesis of a photoreactive (R)-β-phenylalanine is described. In the key step, m-diazirinyl-substituted benzaldehyde is converted to a chiral sulfinimine in a Ti(OEt)4- mediated reaction, followed by diastereoselective enolate addition. The absolute configuration of photo (R)-β-phenylalanine was confirmed by Mosher analysis. The photo amino acid proved to be thermally stable under standard laboratory conditions. Irradiation in toluene afforded cycloheptatriene=norcaradiene valence tautomers, together with carbene benzylation. Quantumchemical calculations indicate a small triplet-singlet gap.

Enantioselective synthesis of the AB ring fragment of gambiertoxin 4B. Implication for the absolute configuration of gambiertoxin 4B and ciguatoxin

1991 ◽  
Vol 32 (35) ◽  
pp. 4505-4508 ◽  
Author(s):  
Toshio Suzuki ◽  
Ohki Sato ◽  
Masahiro Hirama ◽  
Yoshinori Yamamoto ◽  
Michio Murata ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Enantioselective Synthesis ◽  
The Absolute ◽  
Ab Ring

Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part II: Determination of the absolute configuration

2002 ◽  
Vol 13 (13) ◽  
pp. 1411-1415 ◽  
Author(s):  
Giuliana Cardillo ◽  
Serena Fabbroni ◽  
Luca Gentilucci ◽  
Massimo Gianotti ◽  
Rossana Perciaccante ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Enantioselective Synthesis ◽  
The Absolute
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