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Domino Reactions Enable Zn-Mediated Direct Synthesis of Spiro-Fused 2-Oxindole-α-Methylene-γ-Butyrolactones/Lactams from Isatin Derivatives and 2-(Bromomethyl)acrylates.
Molecules
July 2024
Eppley Institute for Research in Cancer and Allied Diseases, Fred & Pamela Buffett Cancer Center, University of Nebraska Medical Center, Omaha, NE 698198, USA.
Isatin-derived spirocyclic cores are found in several biologically active molecules. Here, we report nucleophilic domino reactions for the synthesis of α-methylene-γ-butyrolactone/lactam containing spirocyclic oxindoles. The Zn-mediated one-step reaction accommodates a range of substrates and can be used to rapidly generate focused libraries of highly substituted spirocyclic compound.
View Article and Find Full Text PDFDiscovery of Novel Spiropiperidinyl-α-methylene-γ-butyrolactones as Antifungal and Antitoxin Agents Targeting Oxysterol Binding Protein.
J Agric Food Chem
July 2024
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
Corn ear rot and fumonisin caused by pose a serious threat to food security. To find more highly active fungicidal and antitoxic candidates with structure diversity based on naturally occurring lead xanthatin, a series of novel spiropiperidinyl-α-methylene-γ-butyrolactones were rationally designed and synthesized. The bioassay results indicated that compound showed broad-spectrum activity with EC values falling from 3.
View Article and Find Full Text PDFDiastereoselective allylation-based asymmetric total synthesis of 1,10--guaianolides.
Org Biomol Chem
January 2024
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India.
A Cr(II)-mediated Nozaki-Hiyama allylation of aldehydes with functionalized chiral allylbromolactone paved the way to easily access β-hydroxy-aryl/alkyl-α-methylene-γ-butyrolactones in good yields with high diastereoselectivities. A subsequent undemanding translactonization was orchestrated in the efficient first asymmetric total synthesis of two 1,10--guaianolides as a valuable extension of the strategy developed.
View Article and Find Full Text PDFHeterocycle-Substituted α-Methylene-γ-Butyrolactones Derivatives Synthesis, Antifungal Activity, and 3D-QSAR.
J Agric Food Chem
July 2023
College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, China.
Developing fungicides from active botanical skeletons is one of the effective methods to tackle the resistance of plant pathogens. Based on our previous discoveries, a series of novel α-methylene-γ-butyrolactone (MBL) derivatives containing heterocycles and phenyl rings were designed according to the antifungal molecule carabrone first discovered in plant . The target compounds were synthesized, and the inhibitory activity against pathogenic fungi as well as the mechanism of action were then systematically investigated.
View Article and Find Full Text PDFAsymmetric Synthesis of α-Methylene-γ-Butyrolactones via Tandem Allylboration/Lactonization: a Kinetic Resolution Process.
Angew Chem Int Ed Engl
August 2023
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
The α-methylene-γ-butyrolactone motif is a widely encountered unit in many natural products and pharmaceutical compounds. Herein, a practical and efficient synthesis of α-methylene-γ-butyrolactones from readily available allylic boronates and benzaldehyde derivatives was developed with chiral N,N'-dioxide/Al complex as the catalyst. The key success of this transformation was the kinetic resolution of allylboration intermediate via asymmetric lactonization.
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