139140-13-9Relevant academic research and scientific papers
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.
Natural product rottlerin derivatives targeting quorum sensing
Black, David Stc.,Das, Theerthankar,Kumar, Naresh,Sabir, Shekh,Suresh, Dittu,Wenholz, Daniel,Yu, Tsz Tin
, (2021)
Rottlerin is a natural product consisting of chalcone and flavonoid scaffolds, both of which have previously shown quorum sensing (QS) inhibition in various bacteria. Therefore, the unique rottlerin scaffold highlights great potential in inhibiting the QS
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.
Enantioselective synthesis of orthogonally protected (2R,3R)-(-)- epicatechin derivatives, key intermediates in the de novo chemical synthesis of (-)-epicatechin glucuronides and sulfates
Zhang, Mingbao,Erik Jagdmann Jr.,Van Zandt, Michael,Beckett, Paul,Schroeter, Hagen
, p. 362 - 373 (2013/06/27)
Ten orthogonally protected (-)-epicatechin and 3′- or 4′-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates.
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.
