scholarly journals Efficient Synthesis of Pinoresinol, an Important Lignin Dimeric Model Compound

2021 ◽  
Vol 9 ◽  
Author(s):  
Fengxia Yue ◽  
Wu Lan ◽  
Liming Zhang ◽  
Fachuang Lu ◽  
Runcang Sun ◽  
...  

Pinoresinol is a high-value monolignol-derived lignan used in plant defense and with human health-supporting effects. The synthetic yield and isolation efficiency of racemic pinoresinol from coniferyl alcohol by conventional radical coupling methods is sub-optimal. In this work, a facile and efficient synthetic approach was developed to synthesize pinoresinol with much higher yield. By using 5-bromoconiferyl alcohol, which was synthesized in high yield from 5-bromovanillin, to make 5,5′-bromopinoresinol via a peroxidase-mediated radical coupling reaction takes advantage of the smaller variety of radical coupling products from the 5-substituted monolignol, producing simpler product mixtures from which 5,5′-bromopinoresinol may be readily crystalized with good yield (total yield of 44.1% by NMR; isolated crystalline yield of 24.6%). Hydro-debromination of the crystalline 5,5′-bromopinoresinol to pinoresinol was essentially quantitative. Gram quantities of pinoresinol were conveniently synthesized by using this approach. This simple alternative pathway to make pinoresinol will impact pinoresinol-related research including structural characterization and modification of lignins, as well as clinical applications of pinoresinol and its derivatives.

2021 ◽  
Vol 23 (2) ◽  
pp. 774-779
Author(s):  
Pengfei Niu ◽  
Jingya Yang ◽  
Yong Yuan ◽  
Yongxin Zhang ◽  
Chenxing Zhou ◽  
...  

A redox-neutral decarboxylative radical–radical coupling reaction of heteroaryl methylamines with NHPI esters has been developed by employing a copper complex as a photocatalyst with blue LED irradiation.


Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 860-862 ◽  
Author(s):  
Yun Zhou ◽  
Chunxiao Liu ◽  
Lifeng Wang ◽  
Leng Han ◽  
Shicong Hou ◽  
...  

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.


2019 ◽  
Vol 55 (69) ◽  
pp. 10265-10268 ◽  
Author(s):  
Yao Zhou ◽  
Ya Wang ◽  
Yixian Lou ◽  
Qiuling Song

The first example of denitrogenative radical coupling with 3-aminoindazoles is presented. A diverse array of 1,2-thiobenzonitriles were obtained in good yields with wide substrate scope via oxidative C–N cleavage of 3-aminoindazoles.


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