53690-66-7Relevant academic research and scientific papers
Integrating Metal-Catalyzed C-H and C-O Functionalization to Achieve Sterically Controlled Regioselectivity in Arene Acylation
Serratore, Nicholas A.,Anderson, Constance B.,Frost, Grant B.,Hoang, Truong-Giang,Underwood, Steven J.,Gemmel, Philipp M.,Hardy, Melissa A.,Douglas, Christopher J.
supporting information, p. 10025 - 10033 (2018/07/21)
One major goal of organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation is the most renowned method for the synthesis of aryl ketones, a common structural motif of many pharmaceuticals, agrochemicals, fragrances, dyes, and other commodity chemicals. However, an EAS synthetic strategy is only effective if the desired site for acylation is in accordance with the electronic-controlled regioselectivity of the reaction. Herein we report steric-controlled regioselective arene acylation with salicylate esters via iridium catalysis to access distinctly substituted benzophenones. Experimental and computational data indicate a unique reaction mechanism that integrates C-O activation and C-H activation with a single iridium catalyst without an exogenous oxidant or base. We disclose an extensive exploration of the synthetic scope of both the arene and the ester components, culminating in the concise synthesis of the potent anticancer agent hydroxyphenstatin.
Armeniaspiroles, a new class of antibacterials: Antibacterial activities and total synthesis of 5-chloro-Armeniaspirole A
Couturier, Cedric,Bauer, Armin,Rey, Astrid,Schroif-Dufour, Cosima,Broenstrup, Mark
, p. 6292 - 6296 (2012/10/29)
Armeniaspiroles, a novel class of natural products isolated from Streptomyces armeniacus, are characterized by a novel spiro[4.4]non-8-ene scaffold. Various derivatives of Armeniaspiroles could be obtained by halogenation, alkylation, addition/elimination
Isolation and structural elucidation of armeniaspirols A-C: Potent antibiotics against gram-positive pathogens
Dufour, Cosima,Wink, Joachim,Kurz, Michael,Kogler, Herbert,Olivan, Helene,Sablé, Serge,Heyse, Winfried,Gerlitz, Martin,Toti, Luigi,Nu?er, Antje,Rey, Astrid,Couturier, Cedric,Bauer, Armin,Br?nstrup, Mark
, p. 16123 - 16128 (2013/02/23)
In an antibiotic lead discovery program, the known strain Streptomyces armeniacus DSM19369 has been found to produce three new natural products when cultivated on a malt-containing medium. The challenging structural elucidation of the isolated compounds was achieved by using three independent methods, that is, chemical degradation followed by NMR spectroscopy, a computer-assisted structure prediction algorithm, and X-ray crystallography. The compounds, named armeniaspirol A-C (2-4), exhibit a compact, hitherto unprecedented chlorinated spiro[4.4]non-8-ene scaffold. Labeling experiments with [1-13C] acetate, [1,2-13C2] acetate, and [U-13C] proline suggest a biosynthesis through a rare two-chain mechanism. Armeniaspirols displayed moderate to high in vitro activities against Gram-positive pathogens such as methicillin-resistant S. aureus (MRSA) or vancomycin resistant E. faecium (VRE). As analogue 2 was active in vivo in an MRSA sepsis model, and showed no development of resistance in a serial passaging experiment, it represents a new antibiotic lead structure.
