61892-85-1Relevant articles and documents
A modified synthesis of (Z)-pyrethrolone
Markham, Todd E.,Duggan, Peter J.,Johnston, Martin R.
, p. 99 - 109 (2022/03/16)
An accessible, efficient, and reliable synthesis for the production of (Z)-pyrethrolone remains necessary as previous syntheses suffer from drawbacks including the use of toxic reagents, expensive starting materials and lack of regioselectivity in the production of key intermediates. This work attempts to alleviate the issues of prior syntheses by making use of well-known and regioselective transformations for the efficient synthesis of (Z)-pyrethrolone. Ultimately, (Z)-pyrethrolone is generated in an overall 20% yield over five steps from a cheap, easily accessible starting material using reliable, optimised transformations.
Ruthenium and Formic Acid Based Tandem Catalytic Transformation of Bioderived Furans to Levulinic Acid and Diketones in Water
Dwivedi, Ambikesh D.,Gupta, Kavita,Tyagi, Deepika,Rai, Rohit K.,Mobin, Shaikh M.,Singh, Sanjay K.
, p. 4050 - 4058 (2015/12/26)
Efficient tandem catalytic transformations of bioderived furans, such as furfural, 5-hydroxymethylfurfural (5-HMF), and 5-methylfurfural (5-MF), to levulinic acid (LA) and diketones, 1-hydroxyhexane-2,5-dione (1-HHD), 3-hydroxyhexane-2,5-dione (3-HHD), and hexane-2,5-dione (2,5-HD), was achieved by using water-soluble arene-RuII complexes, containing ethylenediamine-based ligands, as catalysts in the presence of formic acid. The catalytic conversion of furans depends on the catalyst, ligand, formic acid concentration, reaction temperature, and time. Experimental evidence, including time-resolved 1H NMR spectral studies, indicate that the catalytic reaction proceeds first with formyl hydrogenation followed by hydrolytic ring opening of furans. The ruthenium-formic acid tandem catalytic transformation of fructose to diketones and LA was also achieved. Finally, the molecular structures of the four representative arene-RuII catalysts were established by single-crystal X-ray diffraction studies.
Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study
Andersen, Soeren H.,Das, Nalin B.,Joergensen, Ruth D.,Kjeldsen, Gunhild,Knudsen, Jes S.,et al.
, p. 1 - 14 (2007/10/02)
Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.
