An atom-economical and practical synthesis of cis-N-benzenesulfonamide acylaziridines through the Baldwin rearrangement of various N-benzenesulfonamide isoxazolines has been reported. A detailed experimental study revealed the beneficial effect of microwaves and pointed out the crucial role of the temperature in the reaction course. Moderate to good yields and excellent cis stereoselectivities were achieved for 13 examples.
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http://dx.doi.org/10.1021/jo101273d | DOI Listing |
Leuk Res Rep
May 2024
Department of Pathology, Fox Chase Cancer Center, Philadelphia, PA 19111, USA.
Org Process Res Dev
May 2024
School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Ireland D04 N2E2.
A new and highly efficient continuous flow process is presented for the synthesis of aziridines via the thermal Baldwin rearrangement. The process was initially explored using traditional batch synthesis techniques but suffered from moderate yields, long reaction times, and moderate diastereoselectivities. Here we demonstrate that the process can be greatly improved upon its transfer to continuous flow, which afforded the aziridine targets in high yields, short reaction times, and consistently high diastereoselectivities, with the high-throughput process rendering multigram quantities of product in short periods of time.
View Article and Find Full Text PDFPlant Cell Rep
January 2024
Small Grains and Potato Germplasm Research Unit, USDA-ARS, Aberdeen, ID, 83210, USA.
We transferred the Tri6 gene into the elite barley GemCraft via new transformation method through shoot organogenesis and identified the rearrangements of transgenes and phenotypic variations in the transgenic plants. Despite its agronomic and economic importance, barley transformation is still very challenging for many elite varieties. In this study, we used direct shoot organogenesis to transform the elite barley cultivar GemCraft with the RNAi constructs containing Tri6 gene of Fusarium graminearum, which causes fusarium head blight (FHB).
View Article and Find Full Text PDFJ Org Chem
September 2023
College of Biomedical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, People's Republic of China.
A catalyst-free one-pot three-component method of sulfoxonium ylides, nitrosoarenes, and alkynes for the synthesis of highly functionalized di-keto aziridines and alkenes is described. This strategy features the catalyst-free and additive-free approach, the employment of safe, more stable, and readily accessible sulfoxonium ylides, which bear a much wider substrate scope as starting materials. In terms of terminal alkynes, a cascade reaction of nitrone formation/1,3-diploar cycloaddition/Baldwin rearrangement is involved to afford a wide variety of di-keto aziridines.
View Article and Find Full Text PDFGenes Chromosomes Cancer
August 2023
Departments of Pathology and Surgery and Massey Cancer Center, Virginia Commonwealth University School of Medicine, Richmond, Virginia, USA.
Gene fusions involving EWSR1 or FUS as the 5' partner have been reported in a diverse array of sarcomas. Here, we characterize the histopathology and genomics of six tumors harboring a gene fusion between EWSR1 or FUS and POU2AF3, an understudied, putative colorectal cancer predisposition gene. Striking morphologic features reminiscent of synovial sarcoma were observed including a biphasic appearance with variable fusiform to epithelioid cytomorphology and staghorn-type vasculature.
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