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Regioselective Cu-Catalyzed Hydrosilylation of Internal Aryl Alkynes.
Org Lett
January 2025
Department of Chemistry, University of Tennessee, Knoxville, Knoxville, Tennessee 37996, United States.
Construction of vinylsilane building blocks is important for advancing the synthesis of complex small molecules and natural products. Herein, we report a highly regio- and stereoselective copper-catalyzed hydrosilylation of unsymmetrical internal aryl alkynes. The reaction is performed across a broad scope of internal aryl alkynes, providing exclusive access to α-vinylsilane alkenyl arene products, including several silylated small molecule drug analogs.
View Article and Find Full Text PDFBiocatalytic diversification of abietic acid in Streptomyces.
J Ind Microbiol Biotechnol
January 2025
Department of Chemistry, University of Florida, Gainesville, FL, USA.
Biocatalysis provides access to synthetically challenging molecules and commercially and pharmaceutically relevant natural product analogs while adhering to principles of green chemistry. Cytochromes P450 (P450s) are amongst the most superlative and versatile oxidative enzymes found in nature and are desired regio- and stereoselective biocatalysts, particularly for structurally complex hydrocarbon skeletons. We used 10 genome-sequenced Streptomyces strains, selected based on their preponderance of P450s, to biotransform the bioactive diterpenoid abietic acid.
View Article and Find Full Text PDFMicrowave-assisted [3 + 2] cycloaddition reactions of dicyanoepoxides with benzylidene Meldrum's acids.
Org Biomol Chem
January 2025
Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
The [3 + 2] cycloaddition of dicyanoepoxides with benzylidene Meldrum's acid under microwave irradiation and solvent-free conditions was explored for the synthesis of trioxaspirodecanes. This method presents a highly diastereo- and regioselective route to spiro cycloadducts, delivering similar stereoselectivity to conventional reflux in toluene but with shorter reaction times and improved yields.
View Article and Find Full Text PDFPhotoinduced stereoselective reactions using pyridinium salts as radical precursors.
Chem Commun (Camb)
January 2025
Department of Chemistry, Institute of Technology Delhi, Hauz Khas, New Delhi 110-016, India.
Pyridinium salts are amine surrogates that are abundant in nature and the redox active nature of the pyridinium salts allows them to serve as precursors for generating radical species under mild conditions that can be initiated by light, heat or metal catalysis. The stereoselective formation of products has always been a topic of interest for synthetic chemists worldwide. In this context, pyridinium salts can readily undergo single electron reduction to form a neutral radical, and the N-X bond's subsequent fragmentation furnishes the X radical without any harsh reaction conditions.
View Article and Find Full Text PDFStereoselective Sequential Diels-Alder Reactions on a Cyclic Furan Trimer for the Construction of an Asymmetric Scaffold.
Org Lett
January 2025
Institute of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Multiple Diels-Alder reactions are a powerful method to construct large asymmetric scaffolds, but these reactions often produce numerous isomers. We now report a triple Diels-Alder reaction between a cyclic furan trimer and -substituted maleimides, achieving selective synthesis of a single asymmetric tris-adduct. The stereoselectivity of cycloaddition to π-extended furan derivatives was clarified by the experimental analysis of intermediates and theoretical calculations.
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