4541-14-4Relevant academic research and scientific papers
Tandem vinylcyclopropane ring opening/Prins cyclization for the synthesis of 2,3-disubstituted tetrahydropyrans
Reddy, B.V. Subba,Swathi,Bhadra, Manika Pal,Raju, M. Kanaka,Kunwar
, p. 1889 - 1891 (2016)
An efficient synthesis of 2,3-disubstituted tetrahydropyrans from aldehyde and cyclopropyl alkenol has been accomplished using HBF4·OEt2 as a promoter through a tandem vinylcyclopropane ring-opening/Prins cyclization. It is a convenient process to generate a structurally diverse and biologically relevant 2,3-disubstituted tetrahydropyrans in good yields with high selectivity.
Expedient stereoselective synthesis of coronafacic acid through intramolecular Diels-Alder cyclization
Moreau, Benoit,Ginisty, Maryon,Alberico, Dino,Charette, Andre B.
, p. 1235 - 1240 (2007)
(Chemical Equation Presented) A stereoselective synthesis of coronafacic acid, a natural component of the phytotoxin coronatin, was achieved using an intramolecular Diels-Alder reaction as the key step. The triene precursor bearing a substituted diene and a vinylketone as dienophile was synthesized and then tested in the thermal intramolecular cyclization. We have devised a new strategy to assemble the E,Z-diene through the stereoselective aldol reaction of an ester enolate followed by a stereoselective dehydration. Following the thermal cyclization, the corresponding hydrindanone thereby obtained with the desired relative stereochemistry could easily be converted into the natural product. The synthesis of the coronafacic acid was accomplished in six steps in 29% overall yield.
Composition for controlling pine wood nematode containing benzyloxyalcohol
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Paragraph 0055-0056, (2021/06/15)
The present invention relates to a composition for controlling pine nematode comprising a benzyloxyalcohol compound and a method for controlling pine nematode using the same.
Comparing the greenness and sustainability of three routes to an HIV protease inhibitor intermediate
Akakios, Stephanie Gina,Bode, Moira Leanne,Sheldon, Roger Arthur
supporting information, p. 3334 - 3347 (2021/05/21)
The greenness and sustainability of three different routes for the synthesis of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-ol (bis-furan alcohol), an advanced intermediate for a group of HIV protease inhibitors, including the FDA approved darunavir, used in antiretroviral (ARV) therapy, were compared. The method involved a comparison of (i) waste generated using theE-factor and relative to industrial benchmarks using the innovative Green Aspiration Level (iGAL) method, (ii) solvent usage on the basis of solvent intensity (SI) and properties according to the GSK solvent guide, and (iii) Green Motion scores according to the MANE methodology.
C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis
Murugesan, Vetrivelan,Ganguly, Anirban,Karthika, Ardra,Rasappan, Ramesh
supporting information, p. 5389 - 5393 (2021/07/21)
Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.
Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2
Gao, Ziwei,Gou, Jing,Hao, Zhe,Hou, Jing,Li, Chaoqun,Li, Gaoqiang,Xing, Qingzhao,Yu, Binxun
, p. 9563 - 9586 (2021/07/20)
Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.
Nematicidal activity of benzyloxyalkanols against pine wood nematode
Kim, Junheon,Lee, Su Jin,Park, Joon Oh,Yoon, Kyungjae Andrew
, p. 1 - 9 (2021/03/15)
Pine wilt disease (PWD) is caused by the pine wood nematode (PWN; Bursaphelenchus xylophilus) and causes severe environmental damage to global pine forest ecosystems. The current strategies used to control PWN are mainly chemical treatments. However, the continuous use of these reagents could result in the development of pesticide-resistant nematodes. Therefore, the present study was undertaken to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Benzyloxyalkanols (BzOROH; R = C2–C9 ) were synthesized and the nematicidal activity of the synthetic compounds was investigated. Enzymatic inhibitory assays (acetylcholinesterase (AChE) and glutathione S-transferase (GST)) were performed with BzOC8OH and BzOC9OH to understand their mode of action. The benzyloxyalkanols showed higher nematicidal activity than did benzyl alcohol. Among the tested BzOROHs, BzC8OH and BzC9OH showed the strongest nematicidal activity. The LD50 values of BzC8OH and BzC9OH were 246.1 and 158.0 ppm, respectively. No enzyme inhibitory activity was observed for BzC8OH and BzC9OH. The results suggested that benzyloxyalcohols could be an alternative nematicidal agent.
Synthesis of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs
Pal, Ashutosh
, p. 295 - 301 (2021/05/19)
Prodrugs are derivatives of drugs which gives parent drug or release drug when it breaks inside the body by the presence of suitable enzyme, and then exert desired pharmacological effect. For many years, prodrug strategy has been developed enormously to solve many unwanted drug properties. In drug discovery and development, prodrugs have well-known pharmacokinetic effects of pharmacologically nimble products. Almost 10% of drugs permitted whole world are classified as prodrugs, where the application of a prodrug method during initial stages of development is an emergent fashion. Phosphorodiamidates prodrugs are well known anticancer agents particularly against leucomia. To improve the selectivity of the chemotherapeutic agents and reduce systemic toxicity, I herein report different types of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs.
Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants
Bera, Smritilekha,Gupta, Shilpi,Mondal, Dhananjoy
, (2020/02/04)
Organic reactions in the aqueous environment have recently emerged as a promising research area. The generation of nascent-HBr from the slow hydrolysis of the dispersed catalyst, benzyl bromide, with the interior water present in the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.
Ring-closing metathesis approaches towards the total synthesis of rhizoxins
Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.
supporting information, (2020/10/18)
Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.
