85909-04-2Relevant articles and documents
Total Synthesis and Antitrypanosomal Activity of Janadolide and Simplified Analogues
Chung, Jonathan H.,Corcilius, Leo,Geraghty, Kieran,Kaiser, Marcel,Payne, Richard J.,Tang, Arthur H.
supporting information, (2020/04/20)
Janadolide is a cyclic depsipeptide natural product isolated from the marine cyanobacterium Okeania sp. Herein, we describe the total synthesis of janadolide, along with eight simplified analogues, via an efficient solid-phase strategy. Crucial to the synthesis of the natural product was the construction of a key polyketide fragment via an enantioselective (-)-B-chlorodiisopinocampheylborane-mediated reduction and a B-alkyl Suzuki reaction. Janadolide and the simplified analogues exhibited antitrypanosomal activity against pathogenic Trypanosoma brucei rhodesiense and Trypanosoma cruzi parasites.
Aldehydes as potential acylating reagents for oxidative esterification by inorganic ligand-supported iron catalysis
Yu, Han,Wang, Jingjing,Wu, Zhikang,Zhao, Qixin,Dan, Demin,Han, Sheng,Tang, Jiangjiang,Wei, Yongge
supporting information, p. 4550 - 4554 (2019/08/21)
The oxidative esterification of various aldehydes with alcohols could be achieved by a heterogeneous iron(iii) catalyst supported on a ring-like POM inorganic ligand under mild conditions, affording the corresponding esters, including several drug molecules and natural products, in high yields. ESI-MS and control experiments demonstrated that POM-FeV(O) was the active catalytic species and the plausible mechanism was presented. More importantly, the 6th run of the iron catalyst recycles shows only a slight decrease in the yield.
Batch Versus Flow Lithiation–Substitution of 1,3,4-Oxadiazoles: Exploitation of Unstable Intermediates Using Flow Chemistry
Wong, Jeff Y. F.,Tobin, John M.,Vilela, Filipe,Barker, Graeme
supporting information, p. 12439 - 12445 (2019/09/06)
1,3,4-Oxadiazoles are a common motif in pharmaceutical chemistry, but few convenient methods for their modification exist. A fast, convenient, high yielding and general α-substitution of 1,3,4-oxadiazoles has been developed using a metalation-electrophilic trapping protocol both in batch and under continuous flow conditions in contradiction to previous reports which suggest that α-metalation of this ring system results in ring fragmentation. In batch, lithiation is accomplished at an industrially convenient temperature, ?30 °C, with subsequent trapping giving isolated yields of up to 91 %. Under continuous flow conditions, metalation is carried out at room temperature, and subsequent in flow electrophilic trapping gave up to quantitative isolated yields. Notably, lithiation in batch at room temperature results only in ring fragmentation and we propose that the superior mixing in flow allows interception and exploitation of an unstable intermediate before decomposition can occur.
Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides
Deguchi, Toru,Xin, Hai-Long,Morimoto, Hiroyuki,Ohshima, Takashi
, p. 3157 - 3161 (2017/06/09)
Direct catalytic alcoholysis of unactivated amides is one of the most difficult challenges in organic chemistry, and an applicable method for cleaving amides used as directing groups in regioselective functionalization reactions has not been reported. Herein, we report direct catalytic alcoholysis of 8-aminoquinoline amides, which are highly effective directing groups in regioselective functionalization reactions. The reactions proceeded with a simple combination of substrates, air-stable catalysts, and alcohols, affording the corresponding esters in good yields with broad functional group tolerance. Highly chemoselective cleavage of the 8-aminoquinoline amides in the presence of related carbonyl functionalities and preliminary mechanistic studies are also described.
Conversion of alcohols to alkyl esters and carboxylic acids using heterogeneous palladium-based catalysts
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Sheet 3, (2017/04/28)
Disclosed are methods for synthesizing an ester or a carboxylic acid from an organic alcohol. To form the ester one reacts, in the presence of oxygen gas, the alcohol with methanol or ethanol. This reaction occurs in the presence of a catalyst comprising palladium and a co-catalyst comprising bismuth, tellurium, lead, cerium, titanium, zinc and/or niobium (most preferably at least bismuth and tellurium). Alternatively that catalyst can be used to generate an acid from that alcohol, when water is also added to the reaction mix.
CRYSTALLINE FORM OF A BETA-LACTAMASE INHIBITOR
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Paragraph 0113; 0115, (2015/04/28)
This disclosure provides compositions containing solid forms of (2S,5R)-2-(5-(3-aminopropyl)-1,3,4-oxadiazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate, and methods of manufacturing and using these compositions.
Decarbonylative radical coupling of α-aminoacyl tellurides: Single-step preparation of γ-amino and α,β-diamino acids and rapid synthesis of gabapentin and manzacidin A
Nagatomo, Masanori,Nishiyama, Hayato,Fujino, Haruka,Inoue, Masayuki
, p. 1537 - 1541 (2015/01/30)
A new radical-based coupling method has been developed for the single-step generation of various γ-amino acids and α,β-diamino acids from α-aminoacyl tellurides. Upon activation by Et3B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (-)-manzacidin A.
Hydroaminomethylation of Olefins with Aminomethyltrifluoroborate by Photoredox Catalysis
Miyazawa, Kazuki,Koike, Takashi,Akita, Munetaka
, p. 2749 - 2755 (2016/02/18)
A photocatalytic hydroaminomethylation of olefins with N-protected aminomethyltrifluoroborates has been developed. This methodology provides a new strategy for the introduction of a primary aminomethyl group onto electron-deficient C=C bonds. This reaction constitutes a facile entry into synthetically useful γ-aminobutyric acid (GABA) derivatives such as baclofen.
1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS
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Page/Page column 75; 76, (2013/10/21)
β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.
Aerobic oxidation of diverse primary alcohols to methyl esters with a readily accessible heterogeneous Pd/Bi/Te catalyst
Powell, Adam B.,Stahl, Shannon S.
supporting information, p. 5072 - 5075 (2013/10/22)
Efficient aerobic oxidative methyl esterification of primary alcohols has been achieved with a heterogeneous catalyst consisting of 1 mol % Pd/charcoal (5 wt %) in combination with bismuth(III) nitrate and tellurium metal. The Bi and Te additives significantly increase the reaction rate, selectivity, and overall product yields. This readily accessible catalyst system exhibits a broad substrate scope and is effective with both activated (benzylic) and unactivated (aliphatic) alcohols bearing diverse functional groups.
