4386-42-9Relevant academic research and scientific papers
Progress towards viridin: Synthesis of the pentacyclic furanosteroid ring system via o-benzoquinonoid cycloadditions
Souza, Fabio E. S.,Rodrigo, Russell
, p. 1947 - 1948 (1999)
The pentacyclic ring system of viridin is synthesised in nine steps from 4-methylguaicol by means of successive cycloadditions involving o-benzoquinonoid intermediates generated in situ.
Selective carboxylation of substituted phenols with engineered Escherichia coli whole-cells
Peng, Chang,Liu, Yuxue,Guo, Xiaojia,Liu, Wujun,Li, Qing,Zhao, Zongbao K.
, p. 3810 - 3815 (2018/09/21)
Selective carboxylation of substituted phenols is realized in the presence of bicarbonate under ambient pressure by engineered Escherichia coli whole-cells expressing various hydroxybenzoate decarboxylases, leading to their corresponding ortho-hydroxybenzoates. This process may be further developed as an efficient route to upgrade lignin-derived phenolic compounds as valuable building blocks.
Pentacyclic furanosteroids: The synthesis of potential kinase inhibitors related to viridin and wortmannolone
Lang, Yunhui,Souza, Fabio E. S.,Xu, Xinshe,Taylor, Nicholas J.,Assoud, Abdeljalil,Rodrigo, Russell
supporting information; experimental part, p. 5429 - 5439 (2009/12/28)
(Chemical Equation Presented) A regiocontrolled intermolecular Diels-Alder reaction of an o-benzoquinone followed by an intramolecular nitrile oxide cyclization is employed to prepare the BCD fragment of viridin. The AE segment is attached to it by means of an intramolecular Diels-Alder reaction of an o-benzoquinone monoketal generated in situ from tricycle 15 and 5-trimethylsilyl-2E,4E-pentadienol 20. The silyl substituent at C-1 of the pentacyclic product directs the dihydroxylation of the C2-C 3 double bond to its β-face. Various transformations of the 1α-trimethylsilyl-2β,3β-dihydroxy pentacycle into several others with oxygen substituents in ring A are described. One of these products 40 possesses the same structure and relative stereochemistry in rings A, B, and E as that of the natural product wortmannolone 3.
The effect of metal ions on the reaction of hydrogen peroxide with Kraft lignin model compounds
Sun, Yujun,Fenster, Michael,Yu, Annie,Berry, Richard M.,Argyropoulos, Dimitris S.
, p. 667 - 675 (2007/10/03)
Peroxide bleaching is significantly affected by transition and alkaline earth metals. Isolating the effects of different transition and alkaline earth metals on the reactions of peroxide with different representative lignin structures allows the separation of the positive from the negative contributions of these metal ions. In this work, five monomeric or dimeric phenolic lignin model compounds were treated with alkaline hydrogen peroxide in the absence or presence of Mn2+, Cu2+, Fe3+, and Mg2+. We followed the disappearance of the starting material and the progress of demethylation, radical coupling and oxalic acid formation were followed. Transition metals increased the reactivities of all the lignin model compounds with hydrogen peroxide in the order Mn2+ > Cu2+ > Fe3+, which is the same as the order of activity toward peroxide decomposition while Mg2+ stabilized the system. Demethylation, radical coupling, and oxalic acid formation were all increased by the presence of transition metals in the system and decreased by the addition of Mg2+. The acceleration of the total degree of reaction and of the demethoxylation reactions improves peroxide bleaching, but the increase in the radical coupling reactions can affect the further bleachability of pulp while the increase in the formation of oxalic acid could lead to a greater probability of scaling.
