Reverse regioselectivity: The first catalytic asymmetric C-1 functionalization of 1,3-dicarbonyl compounds by an aldol reaction is described, which regioselectively affords 6-hydroxyhexane-2,4-dione derivatives as the only product with high optical purity of up to 93 % ee. Furthermore, this method provides a facile access to enantioenriched oxygen-containing spirooxindoles and spirobutyrolactones from simple commercial available starting materials (see scheme).
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http://dx.doi.org/10.1002/chem.201201874 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Changchun Institute of Applied Chemistry Chinese Academy of Sciences: Chang Chun Institute of Applied Chemistry Chinese Academy of Sciences, Jilin Province Key Lab of Green Chemistry and Process, CHINA.
A modular approach was developed for the first catalytic asymmetric total syntheses of naturally occurring C30 terpene quinone methides and their non-natural stereoisomers, which feature the presence of an unprecedented spiro[4.4]nonane-containing 6-6-6-5-5-3 hexacyclic skeleton. Resting on a chiral phosphinamide-catalyzed enantioselective reduction of 2,2-disubstituted cyclohexane-1,3-dione, a concise route for the synthesis of enantioenriched 6-6 bicyclic fragment was developed.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.
The successful implementation of a cascade reaction involving a cyclobutyl unit has posed a significant challenge in achieving ring-retentive functionalization because of the ring's sacrificial tendency. Herein, we have accomplished a cinchona-derived squaramide-catalyzed cascade reaction sequence, encompassing the desymmetrization of cyclobutanone, followed by an aldol reaction and, subsequently, a 1,4-addition step. This overall process offers a viable strategy to access architecturally fascinating oxa-spirocycles fused with cyclobutanone motifs in good yields with high optical purity.
View Article and Find Full Text PDFSci Rep
January 2025
Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria, 21321, Egypt.
New formyl indole derivatives based on thiobarbituric acid were designed for targeting parasitological applications. The new compounds (5-((1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3a), and 5-((1-benzyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (3b) were synthesized as thioxodihydropyrimidine derivatives via aldol condensation reaction. The structures of the synthesized compounds were confirmed based on their spectral data via FT-IR, H and C NMR spectral characterization.
View Article and Find Full Text PDFChemistry
December 2024
Southern University of Science and Technology, Chemistry, 1088 Xueyuan Avenue, 518055, Shenzhen, CHINA.
The convergent total synthesis of ixabepilone and its analogues in a 13-step longest linear sequence is reported. The crucial chiral centers at challenging C3-O, C8-C and C15-N positions on the scaffold of the ixabepilone were installed via highly efficient asymmetric hydrogenations (up to 95% yield and up to 99% e.e.
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