Co-reporter:Wenling Li, Tao Dong, Peilan Chen, Xiaolin Liu, Meijie Liu, Xiaoqian Han
Tetrahedron 2017 Volume 73, Issue 21(Issue 21) pp:
Publication Date(Web):25 May 2017
DOI:10.1016/j.tet.2017.04.021
The simple synthesis of (±)-parthenostilbenins A and B and (±)-quadrangularins A and B, as well as several unnatural resveratrol dimers, was successfully accomplished for the first time. Moreover, (±)-restrytisols B, (±)-leachianols F and G were efficiently prepared with higher yields compared with those in the literatures. The regioselective oxidative coupling reactions of 3,5-dibromo-resveratrol catalyzed by different enzymes in various solvent systems were used as key steps. The coupling mechanisms for the formation of distinct dimeric skeletons were also proposed.Download high-res image (119KB)Download full-size image
Co-reporter:Wenling Li, Peilan Chen, Yadong Yang, Xiaolin Liu, Tao Dong
Tetrahedron 2016 Volume 72(Issue 1) pp:210-215
Publication Date(Web):7 January 2016
DOI:10.1016/j.tet.2015.11.028
FeCl3-catalyzed oxidative coupling reactions of protected resveratrol in the different solvents directly constructed three distinct dimeric skeletons, which were converted into several oligostilbenes through the respective global deprotections. The solvent effects on the structures of coupling products and reaction pathways involved were briefly discussed.
Co-reporter:Wenling Li;Qian Liu;Hao Liu;Peilan Chen;Xi Yang ;Yingying Liu
Chinese Journal of Chemistry 2015 Volume 33( Issue 7) pp:717-722
Publication Date(Web):
DOI:10.1002/cjoc.201500054
Abstract
The regioselective effects of tert-butyl or bromine as the position-protecting group of feruloytyamide on the oxidative coupling reactions for the synthesis of natural (±)-canabisin D were investigated in detail. The coupling yield of 8-8-coupled aryldihydronaphthalene product of 5-Br-feruloytyamide was higher than that of tert-butyl substituted precursor under FeCl3·6H2O-acetone-water oxidative condition.
Co-reporter:Wenling Li, Shixia Yang, Teng Lv and Yadong Yang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 14) pp:2273-2279
Publication Date(Web):03 Feb 2014
DOI:10.1039/C3OB42456A
We report the first synthesis of a natural (±)-gnetulin and an unnatural analogue of (±)-gnemonol M by using the regioselective oxidative coupling reactions of 5-tert-butyl-isorhapontigenin as the key step. Both the effects of different enzyme-catalyzed systems on the structures of coupling products and structural transformations of coupling products in the presence of several Lewis acids were systematically investigated.
Co-reporter:Wenling Li;Hao Liu;Jingyan Xu;Peng Zang;Qian Liu;Wenbo Li
European Journal of Organic Chemistry 2014 Volume 2014( Issue 16) pp:3475-3482
Publication Date(Web):
DOI:10.1002/ejoc.201301825
Abstract
A regioselective biomimetic oxidative cyclization strategy for the construction of aryldihydronaphthalene skeletons has been developed as an efficient synthetic approach to the preparation of natural 8-8-cyclic diferulic acid and canabisin D. The oxidative coupling of ethyl 5-tert-butylferulate catalyzed by different oxidants yielded tetrahydrofuran or dibenzylidenesuccinate-type 8-8-coupling products, which were subsequently subjected to acid-catalyzed cyclization to produce several isomeric trans-aryldihydronaphthalenes. The reaction mechanisms for all the cyclization reactions have also been proposed.
Co-reporter:Yadong Yang, Qian Liu, Peilan Chen, Wenling Li
Tetrahedron Letters 2014 Volume 55(Issue 32) pp:4455-4457
Publication Date(Web):6 August 2014
DOI:10.1016/j.tetlet.2014.06.046
Several 8-8-coupled tetraarylfuran-type oligostilbenes were prepared through FeCl3·6H2O-catalyzed regioselective oxidative couplings of protected resveratrol precursors. The global deprotection of the coupling dimers in a one-pot reaction yielded (±)-pallidol instead of the targets (±)-restrytisol B and (±)-tricuspidatol A.
Co-reporter:Wenling Li, Shixia Yang, Teng Lv and Yadong Yang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 14) pp:NaN2279-2279
Publication Date(Web):2014/02/03
DOI:10.1039/C3OB42456A
We report the first synthesis of a natural (±)-gnetulin and an unnatural analogue of (±)-gnemonol M by using the regioselective oxidative coupling reactions of 5-tert-butyl-isorhapontigenin as the key step. Both the effects of different enzyme-catalyzed systems on the structures of coupling products and structural transformations of coupling products in the presence of several Lewis acids were systematically investigated.
![Indeno[2,1-a]indene-1,3,6,8-tetrol,4b,5,9b,10-tetrahydro-5,10-bis(4-hydroxyphenyl)-, (4bR,5R,9bR,10R)-](http://img.cochemist.com/ccimg/105100/105037-88-5.png)
![Indeno[2,1-a]indene-1,3,6,8-tetrol,4b,5,9b,10-tetrahydro-5,10-bis(4-hydroxyphenyl)-, (4bR,5R,9bR,10R)-](http://img.cochemist.com/ccimg/105100/105037-88-5_b.png)
