139140-13-9Relevant articles and documents
Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II
Adler, Marc J.,Baldwin, Steven W.
, p. 5075 - 5079 (2009)
Herein is reported an efficient method for the synthesis of 2,2-dimethyl-2H-chromenes in a single step from the corresponding phenol and 3-methyl-2-butenal via microwave irradiation in CDCl3. This protocol features a mild reaction environment (neutral, no added catalyst) which yields regioselective formation of the chromene and displays tolerance toward acid- and base-sensitive protecting groups.
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.,Ho, Kitty K. K.,Bhadbhade, Mohan,Ball, Graham E.,Black, David Stc.,Kumar, Naresh
, p. 1190 - 1199 (2019/05/17)
Rottlerin (1) is a potent protein kinase C δinhibitor that possesses a wide range of biological activities. However, the potential of this molecule to be developed as a drug has been restricted by its limited availability. We report herein a gram scale quantity synthesis of rottlerin in a five-step synthetic route that can be completed within 2 days. The methodology was extended by the reaction of the key aminochromene intermediate (15) with various electron-rich arenes, forming novel unsymmetrical methylene-bridged compounds. The X-ray crystal structure revealed the boomerang shape of this kind of molecule for the first time. The direct transformation of rottlerin (1) into the natural product, isorottlerin (35), was observed for the first time, and we named this transformation the "isorottlerin change". In addition, the antibacterial activities of rottlerin (1) and new rottlerin analogues 32-34 were examined against Staphylococcus aureus. The compounds showed MIC values as low as 2.0 μM, which were comparable to the clinically used antibiotic gentamicin.
Selective cleavage of tert-butyldimethylsilylethers ortho to a carbonyl group by ultrasound
De Groot, Alex H.,Dommisse, Roger A.,Lemière, Guy L.
, p. 1541 - 1549 (2007/10/03)
A general method for the selective cleavage of tert- butyldimethylsilylethers ortho to a carbonyl group is established by sonication of a 0.1 M solution of the substrate in 1/1 (v/v) CH3OH/CCl4. Other phenolic tert-butyldimethylsilylethers are unaffected. This reaction performed on flavanoids is completed within 3 h and no special workup is required. Other substrates are also investigated and a mechanism is proposed. (C) 2000 Elsevier Science Ltd.
