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Palladium-Catalyzed Reductive and Redox-Neutral Cyclization Approach to the Southern Core of Avermectins.
Org Lett
December 2024
Omura Satoshi Memorial Institute and Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
The avermectins make up a biologically relevant class of complex natural products that continue to inspire the development of new strategies in chemical synthesis. Herein, we disclose a concise synthesis of the southern core of avermectin aglycon. The key hydrobenzofuran was forged by either reductive cyclization or cycloisomerization, both using a cationic palladium precatalyst.
View Article and Find Full Text PDFA rapid pathway to molecular complexity: a palladium-catalyzed six-fold domino process to access polycyclic frameworks.
Chem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology, Hyderabad, Kandi, Sangareddy, 502284, Telangana, India.
Herein, we present a hitherto unexplored efficient strategy for rapidly constructing structurally constrained and intriguing polycyclic frameworks with two adjacent quaternary centers. Remarkably, this becomes possible through palladium-catalyzed six-fold domino crossover annulations of simple 1,2-bis(2-bromoaryl)ethynes and 1,2-diarylethynes. Notably, this approach demonstrates the synthesis of both C-symmetric and unsymmetric polycyclic products.
View Article and Find Full Text PDFTailored chiral phosphoramidites support highly enantioselective Pd catalysts for asymmetric aminoalkylative amination.
Nat Commun
December 2024
Key Laboratory of Precision and Intelligent Chemistry and Department of Chemistry, University of Science and Technology of China, 230026, Hefei, P. R. China.
Even though tuning electronic effect of chiral ligands has proven to be a promising method for designing efficient catalysts, the potential to achieve highly selective reactions by this strategy remains largely unexplored. Here, we report a palladium-catalyzed enantioselective ring-closing aminoalkylative amination of aminoenynes enabled by rationally tuning the remote electronic property of 1,1'-binaphthol-derived phosphoramidites. With a tailored 6,6'-CN-substituted 1,1'-binaphthol-derived phosphoramidite as a ligand, a broad range of aromatic amines are compatible with this reaction, allowing the efficient synthesis of a series of enantioenriched exocyclic allenylamines bearing saturated N-heterocycles with up to >99% enantiomeric excess.
View Article and Find Full Text PDFPalladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines.
Org Lett
December 2024
School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China.
The functionalization of the C-Cl bond in unactivated aryl chlorides under mild conditions presents a significant challenge. We disclose a general protocol for constructing both partially and entirely unsymmetrical tertiary phosphines through the Pd/keYPhos-catalyzed coupling of aryl chlorides with secondary phosphines under mild conditions. The reaction exhibits excellent functional group tolerance and broad substrate scopes.
View Article and Find Full Text PDFConcise Asymmetric Total Syntheses of (+)-Dihydropleurotinic Acid and (-)-Pleurotin, Enabling Rapid Late-Stage Diversification.
JACS Au
November 2024
Laboratory of Medicinal Chemical Biology, Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren'ai Road, Suzhou 215123, China.
(-)-Pleurotin () and (+)-dihydropleurotinic acid () are benzoquinone meroterpenoids isolated from fungal sources with powerful antitumor and antibiotic activities. Concise asymmetric total syntheses of the stereochemically pure (+)-dihydropleurotinic acid () and (-)-pleurotin () from the chiral pool ()-Roche ester-derived vinyl bromide have been achieved in 12 and 13 longest linear steps, respectively. The key transformations feature a Michael addition/alkylation cascade reaction to forge three contiguous stereocenters matched with the natural products, a PtO-catalyzed stereoselective reduction of olefin to generate the correct stereocenter at C3, a palladium-catalyzed Negishi cross-coupling between triflate and zinc reagent to introduce the redox-sensitive para-quinone moiety, and a hydroboration/copper-catalyzed carboxylation sequence to incorporate the vital carboxyl group.
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