Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host
Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m?1 s?1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.
Petroselli, Manuel,Rebek, Julius,Yu, Yang
supporting information
p. 3284 - 3287
(2021/02/05)
Radical Reactions in Cavitands Unveil the Effects of Affinity on Dynamic Supramolecular Systems
Radical reduction of alkyl halides and aerobic oxidation of alkyl aromatics are reported using water-soluble container compounds (1 and 2). The reductions involve α,ω-dihalides (4-8 and 10) with radical initiators in cavitand hosts with varied binding affinities. Product distributions lead to general guidelines for the use of dynamic supramolecular systems with fast reactions. The binding of guest substrates in the hosts must show high affinities (Ka> 103M-1) to ensure that the reactions take place under confinement in the containers.
Synthesis and biological characterization of (Z)-9-heptadecenoic and (Z)-6-methyl-9-heptadecenoic acids: Fatty acids with antibiotic activity produced by Pseudozyma flocculosa
Difficulties in isolating and purifying antibiotic fatty acids from culture filtrates of Pseudozyma flocculosa, a biocontrol agent against powdery mildew, have been limiting factors in studying the properties and understanding the mode of action of the biocontrol agent. We report a new protocol for synthesizing (Z)-9-heptadecenoic and for the first time synthesis of (Z)-6-methyl-9-heptadecenoic acids, two antibiotic fatty acids produced by P. flocculosa. This allowed reproducible and quantifiable means of assaying biological activity of the molecules. In these bioassays, both molecules exhibited antifungal activity corresponding to their expected potency. These new developments should facilitate further studies aimed at deciphering the ecological properties of P. flocculosa.
Avis,Boulanger,Belanger
p. 987 - 1000
(2007/10/03)
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