The Highly Selective Synthesis of 5-Methy Vanillin from the By-product in Vanilla Industry and The Scent Influence for Vanillin

Author(s):  
Haifang Mao ◽  
Hongzhao Wang ◽  
Ting Tang ◽  
Shi Qixuan ◽  
Haiyan Yu ◽  
...  

Aimed on comprehensive utilization of useless by-product, a highly selective method was proposed for 5-methyl vanillin (M-Vanillin) production by employing the o-Vanillin which is a useless by-product in vanillin industry...

2021 ◽  
Vol 17 ◽  
pp. 234-244
Author(s):  
Jean C Kazmierczak ◽  
Roberta Cargnelutti ◽  
Thiago Barcellos ◽  
Claudio C Silveira ◽  
Ricardo F Schumacher

We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of β-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto–enol tautomers was possible, revealing them as significant intermediates for the mechanism elucidation.


Planta Medica ◽  
2014 ◽  
Vol 80 (10) ◽  
Author(s):  
JA Marañón ◽  
L de los Santos ◽  
C Lozano ◽  
E Caballero ◽  
F Galán-Estella

Author(s):  
William Finnigan ◽  
Lorna J. Hepworth ◽  
Nicholas J. Turner ◽  
Sabine Flitsch

As the enzyme toolbox for biocatalysis has expanded, so has the potential for the construction of powerful enzymatic cascades for efficient and selective synthesis of target molecules. Additionally, recent advances in computer-aided synthesis planning (CASP) are revolutionizing synthesis design in both synthetic biology and organic chemistry. However, the potential for biocatalysis is not well captured by tools currently available in either field. Here we present RetroBioCat, an intuitive and accessible tool for computer-aided design of biocatalytic cascades, freely available at retrobiocat.com. Our approach uses a set of expertly encoded reaction rules encompassing the enzyme toolbox for biocatalysis, and a system for identifying literature precedent for enzymes with the correct substrate specificity where this is available. Applying these rules for automated biocatalytic retrosynthesis, we show our tool to be capable of identifying promising biocatalytic pathways to target molecules, validated using a test-set of recent cascades described in the literature.


2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.


2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.


2019 ◽  
Vol 16 (9) ◽  
pp. 700-704
Author(s):  
Jitander K. Kapoor ◽  
Loveena Arora ◽  
Om Prakash

Various arylethanones including electron-rich aromatic ketones such as o-hydroxyacetophenone and its p-isomer underwent selective side-chain α,α-dibromination using a heterogeneous system consisting of four molar equivalents of copper(II) bromide in chloroform-ethyl acetate under reflux. This study provides the cleanest method for the selective synthesis of several synthetically useful α,α-dibromoketones which are otherwise difficult to prepare.


2015 ◽  
Vol 2 (3) ◽  
pp. 319-338 ◽  
Author(s):  
Mercedesz Kiss ◽  
Attila Takacs ◽  
Laszlo Kollar

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