157065-45-7Relevant academic research and scientific papers
A practical method to stereospecifically synthesize trans-stilbene derivatives
Jian, Yujuan,Sun, Gaojun,Li, Jiaming,Su, Dan,Li, Chuanrun,Zhong, Guochen
scheme or table, p. 1423 - 1428 (2011/10/31)
A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane (BTMS), which was driven by tetrabutylammonium fluoride (TBAF) in THF. At the same time a plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. Also this method was employed to synthesize three precursors of natural products with excellent yields, which demonstrated that this method is much efficient and practical in the synthesis of some natural products. A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane, which was driven by tetrabutylammonium fluoride in THF. A plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. This method was employed to synthesize three precursors of natural products with excellent yields. Copyright
Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 417 - 421 (2007/10/03)
The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C11H23CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields. The dehydroxylation of these compounds through the corresponding mesylates 5 or directly from benzylic derivatives by catalytic hydrogenation, afforded compounds 6, which are finally demethylated to yield 5-alkyl-3,5-dihydroxyresorcinols, such as olivetol (7a), grevillol (7b), 1,3-dihydroxy-5-propylbenzene (7c), or dihydropinosilvine (7d). Dehydration of alcohol derivatives 4 followed by demethylation led to hydroxylated stilbene-type structures, such as pinosilvine (9d), resveratrol (9e), or piceatannol (9f), which in some cases can be hydrogenated to give saturated molecules such as combretastanin B-4 tetramethyl ether (6f) or chrysotobibenzyl (6g). Finally, when the naphthalene-catalyzed lithiation of compound 3 was performed in the presence of other electrophiles [Me3SiCl, t-BuCHO, CH3(CH2)4CHO, 4-Me3SiOC6H4CHO, (CH2)5CO, PhN = C = O, PhN = CHPh], the expected reaction products 12 were isolated, after hydrolysis.
Preparation of Cyclohexane-1,3-dione Herbicide Precursors by Birch Reduction of 3,5-Dimethoxyphenyl-Substituted Silane Derivatives
Ali, Abdelselam S.,Liepa, Andris J.,Thomas, Mark D.,Wilkie, John S.,Winzenberg, Kevin N.
, p. 1205 - 1210 (2007/10/02)
Birch reduction of the silane derivatives (3a-d), prepared from Grignard cross-coupling reactions, afforded the cyclohexane-1,3-dione derivatives (5a-d) after acid hydrolysis.Compounds (5a-d) are precursors to silicon-containing herbicides of the general
