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Keywords = Swern oxidation

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4 pages, 652 KB  
Short Note
3-Methyl-2-((methylthio)methyl)but-2-enal
by Huaxuan Zhang and Xingang Xie
Molbank 2025, 2025(3), M2037; https://doi.org/10.3390/M2037 - 16 Jul 2025
Viewed by 1435
Abstract
During the Swern oxidation of 3-methylbut-3-en-1-ol, an unexpected C-C bond formation product, 3-methyl-2-(methylthio)but-2-enal, was obtained. Its structure was characterized using 1H-NMR, 13C-NMR, and HRMS. Based on the classical Swern oxidation mechanism and the unique structural features of the substrate, we propose [...] Read more.
During the Swern oxidation of 3-methylbut-3-en-1-ol, an unexpected C-C bond formation product, 3-methyl-2-(methylthio)but-2-enal, was obtained. Its structure was characterized using 1H-NMR, 13C-NMR, and HRMS. Based on the classical Swern oxidation mechanism and the unique structural features of the substrate, we propose a plausible reaction pathway. This discovery not only provides insights into the selection of oxidation conditions for 1, 1-disubstituted homoallylic alcohols with analogous structures but also offers a viable synthetic route for the preparation of compounds containing the 3-methyl-2-(methylthio)but-2-enal motif. Full article
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23 pages, 592 KB  
Review
Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product
by Adriana Pabón, Gustavo Escobar, Esteban Vargas, Víctor Cruz, Rafael Notario, Silvia Blair and Fernando Echeverri
Molecules 2013, 18(3), 3356-3378; https://doi.org/10.3390/molecules18033356 - 14 Mar 2013
Cited by 25 | Viewed by 10100
Abstract
Solanum nudum Dunal steroids have been reported as being antimalarial compounds; however, their concentration in plants is low, meaning that the species could be threatened by over-harvesting for this purpose. Swern oxidation was used for hemisynthesis of diosgenone (one of the most active [...] Read more.
Solanum nudum Dunal steroids have been reported as being antimalarial compounds; however, their concentration in plants is low, meaning that the species could be threatened by over-harvesting for this purpose. Swern oxidation was used for hemisynthesis of diosgenone (one of the most active steroidal sapogenin diosgenin compounds). Eighteen structural analogues were prepared; three of them were found to be more active than diosgenone (IC50 27.9 μM vs. 10.1 μM, 2.9 μM and 11.3 μM). The presence of a 4-en-3-one grouping in the A-ring of the compounds seems to be indispensable for antiplasmodial activity; progesterone (having the same functional group in the steroid A-ring) has also displayed antiplasmodial activity. Quantitative correlations between molecular structure and bioactivity were thus explored in diosgenone and several derivatives using well-established 3D-QSAR techniques. The models showed that combining electrostatic (70%) and steric (30%) fields can explain most variance regarding compound activity. Malarial parasitemia in mice became reduced by oral administration of two diosgenone derivatives. Full article
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6 pages, 35 KB  
Article
Swern Oxidation of Bicyclo[2.2.1]hept-5-ene-2,3-diol and Its Pyrazine-fused Derivatives: An Improved Synthesis of Bicyclo[2.2.1]hept-5-ene-2,3-dione and An Unexpected Ring-Opening Reaction
by Tomoshige Kobayashi and Sayuri Kobayashi
Molecules 2000, 5(9), 1062-1067; https://doi.org/10.3390/50901062 - 9 Sep 2000
Cited by 14 | Viewed by 10832
Abstract
An improved synthesis of bicyclo[2.2.1]hept-5-ene-2,3-dione by Swern oxidation of bicyclo[2.2.1]hept-5-ene-2,3-diol, and an unexpected ring-opening reaction by the Swern oxidation of pyrazine-fused congeners are described. Full article
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