An organocatalyzed stereoselective domino reaction as a facile approach to multicyclic spirooxindole derivatives bearing two stereogenic quaternary carbon atoms is reported. The alkyl-substituted chiral thiourea catalyst was efficient for the reaction to tolerate a wide range of substrates, furnishing a new class of spirooxindole derivatives bearing an ,-acetal-fused tricyclic skeleton or tetrahydroxanthone moiety in moderate to good yields with good to excellent selectivities. The products generated from this method have promising anticancer activities.
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http://dx.doi.org/10.1021/acs.orglett.3c00705 | DOI Listing |
Org Biomol Chem
January 2025
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.
As one of the main fragments in medical drugs, spirooxindole has received considerable attention from organic and medicinal chemists. In the past few decades, chemists have been searching for more straightforward and efficient methods to produce compounds containing a spirooxindole fragment. In this regard, isatin-derived Morita-Baylis-Hillman (MBH) carbonates have been widely used as versatile building blocks for the synthesis of spirooxindole structures.
View Article and Find Full Text PDFMonoterpene indole alkaloids (MIAs) are a large, structurally diverse class of bioactive natural products. These compounds are biosynthetically derived from a stereoselective Pictet-Spengler condensation that generates a tetrahydro-β-carboline scaffold characterized by a 3 stereocenter. However, a subset of MIAs contain a non-canonical 3 stereocenter.
View Article and Find Full Text PDFChemistry
December 2024
Department of Chemistry, Indian Institute of Technology Kanpur, Uttar Pradesh, Kanpur, 208016, India.
Herein, we report a copper-catalyzed enantioselective formal (3+3) and (3+2) cycloaddition reaction of isatin-derived tertiary propargylic esters with N,N-dimethylbarbituric acid and 4-hydroxycoumarins, respectively. In this process, the tertiary propargylic ester serves as both C3- and C2-synthons, facilitating the synthesis of optically active spirooxindole-pyran and furan scaffolds featuring an all-carbon quaternary stereocenter. The reaction delivers these spirocyclic frameworks in good yields with high enantioselectivities.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Sichuan Provincial Key Laboratory of Quality and Innovation Research of Chinese Materia Medica, Sichuan Academy of Chinese Medicine Sciences, Chengdu 610041, P. R. China.
Although there have been various reviews on the asymmetric construction of C3-spirooxindoles, there is a scarcity of reviews focusing on the asymmetric organocatalytic synthesis of C3-spiro-cyclopentaneoxindole derivatives. This particular scaffold has garnered significant attention from synthetic chemists due to its relevance in medicinal chemistry. In this review, we provide an overview of recent advancements in the asymmetric organocatalytic synthesis of various C3-spiro-cyclopentaneoxindoles using organic catalysts.
View Article and Find Full Text PDFMolecules
November 2024
Institut für Organische Chemie und Makromolekulare Chemie, Mathematisch-Naturwissenschaftliche Fakultät, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
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