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The Sc(OTf)-catalyzed reaction of 2-aminobenzamide with -substituted pyrrole-2-carboxaldehyde proceeded well to give a tetracyclic skeleton consisting of dihydroquinazolin-4-one and 1,2-dihydropyrrolo[1,2-]pyrazine regioselective double cyclodehydrations where two heterocyclic rings (quinazolinone and pyrazine) were sequentially constructed through the formation of three C-N bonds.
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http://dx.doi.org/10.1039/d5ob00580a | DOI Listing |
Chem Pharm Bull (Tokyo)
August 2025
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-cho, Tokushima 770-8514, Japan.
Prealnumycin B is an aromatic polyketide characterized as a reduced form of prealnumycin with a 6S-alcohol. As an extension of our earlier work on the synthesis of prealnumycin, the C7-C8 double bond was hydrogenated using Wilkinson's catalyst, and the C6 carbonyl group was stereoselectively reduced via asymmetric transfer hydrogenation with the (S,S)-Ts-DENEB catalyst, where the use of methanol as a solvent was crucial for achieving high regioselectivity. By comparing its spectroscopic data with those of the natural isolate, the absolute configuration of prealnumycin B was determined to be 1R,6S.
View Article and Find Full Text PDFScience
August 2025
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs and Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, S
Efficient asymmetric epoxidation reactions have been developed for both the head end and tail end double bonds of farnesol, greatly facilitating the synthesis of terpenoid natural products. However, the lack of methods for direct asymmetric epoxidation of the relatively inert internal alkene of farnesol has posed major challenges in the synthesis of many terpenoids. In this study, we describe the engineering of an epoxidase capable of selectively epoxidizing the internal alkene of farnesol with high regioselectivity and enantioselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 321004 Jinhua, China.
Over the past decade, the design of new radical reactions has emerged as an increasingly powerful strategy for constructing complex molecular scaffolds, typically characterized by predictable yet divergent reaction outcomes, a wide range of radical precursors, and various modes of initiation. Notably, radical cascade addition reactions serve as an efficient and practical strategy for constructing cyclic compounds. The scope of intermolecular radical acceptors is usually limited to C-C double or triple bonds.
View Article and Find Full Text PDFOrg Biomol Chem
July 2025
Department of Chemistry, College of Engineering and Technology, SRM Institute of Science and Technology, Kattankulathur, 603 203 Chennai, Tamil Nadu, India.
Regioselective (3 + 2) cycloaddition reactions of zerumbone with nitrile oxides and azomethine ylides are developed for the first time. Direct functionalization of the C10-C11 double bond in zerumbone is unique. ZI-8, ZI-9, and ZI-10 exhibited substrate-driven dimer formation, whereas ZI-9 and ZI-10 exhibited solid-state conformational variability.
View Article and Find Full Text PDFChemistry
August 2025
Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK.
A range of aryl- and alkyl- substituted alkynes has been shown to insert regio-selectively into the Sn─Si bond of the electron-rich aryl(silyl)stannylene, ArSnSi(SiMe) (Ar = 2,6-MesCH, Mes = 2,4,6-MeCH) to generate a series of vinyl-stannylene products. In all cases, the product features a syn arrangement of Sn and Si-containing groups about the resulting carbon-carbon double bond; in the case of unsymmetrical alkynes, the more sterically bulky group is exclusively incorporated in the 1-position (i.e.
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