- Access to "friedel-Crafts-Restricted" tert -alkyl aromatics by activation/methylation of tertiary benzylic alcohols
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Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
- Hartsel, Joshua A.,Craft, Derek T.,Chen, Qiao-Hong,Ma, Ming,Carlier, Paul R.
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experimental part
p. 3127 - 3133
(2012/05/20)
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- Chromanol derivatives - A novel class of CETP inhibitors
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Based on our former development candidate BAY 38-1315, optimization efforts led to the discovery of a novel chemical class of orally active cholesteryl ester transfer protein (CETP) inhibitors. The chromanol derivative 19b is a highly potent CETP inhibitor with favorable pharmacokinetic properties suitable for clinical studies. Chemical process optimization furnished a robust synthesis for a kilogram-scale process.
- Vakalopoulos, Alexandros,Schmeck, Carsten,Thutewohl, Michael,Li, Volkhart,Bischoff, Hilmar,Lustig, Klemens,Weber, Olaf,Paulsen, Holger,Elias, Harry
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scheme or table
p. 488 - 491
(2011/02/27)
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- SYNTHESIS OF A CARBOCYCLIC ANALOG OF QUERCETIN VIA A BARBIER REACTION
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A six-step synthetic route to the carbocyclic flavonoid 2 is described.The key step involves a 1,4-addition of a tertiary bromide to a α,β-unsaturated ester by the Barbier reaction.
- Shih, Neng-Yang,Mangiaracina, Pietro,Green, Michael J.,Ganguly, Ashit K.
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p. 5563 - 5566
(2007/10/02)
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- Antiestrogens. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 1,1,2,2-Tetraalkyl-1,2-diphenylethanes
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Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73*108 and 0.67*108 M-1, respectively.In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse.They strongly inhibited (73percent) the estrone-stimulated mouse uterine growth.Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).
- Hartmann, Rolf W.,Kranzfelder, Gerhard,Angerer, Erwin, v.,Schoenenberger, Helmut
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p. 841 - 848
(2007/10/02)
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