A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse -2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037326 | PMC |
http://dx.doi.org/10.3390/molecules25030648 | DOI Listing |
Chemistry
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.
View Article and Find Full Text PDFOrg Lett
December 2024
School of Pharmacy, Jiangsu University, Zhenjiang 212013, China.
Utilizing enzymes as biocatalysts, an alternative strategy has been developed for the highly enantioselective synthesis of chiral 2,3-dihydrobenzofuran (2,3-DHB) esters via the dynamic kinetic resolution of 2,3-dihydro-3-benzofuranols, which are generated from an intramolecular Aldol reaction. This protocol provides easy access to a series of 2,3-DHB ester derivatives, prodrugs, and allows for functional group transformations. Biological evaluation also indicates that some of the products exhibit potent anti-inflammatory activity.
View Article and Find Full Text PDFOrg Lett
December 2024
Molecular Synthesis Center & Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
A regiodivergent strategy for the asymmetric diversity-oriented synthesis of spirooxindoles via organocatalytic cascade reactions is developed. Two regioselective pathways can be precisely controlled with different aminocatalysts in the reaction of 2-hydroxycinnamaldehydes and β,β-disubstituted 3-alkylidene oxindoles. The cascade vinylogous Michael/oxa-Michael/aldol reactions gave spiro-bridged oxindoles bearing two adjacent quaternary stereocenters, while the cascade oxa-Michael/Michael reactions gave spirooxindoles.
View Article and Find Full Text PDFMacromol Rapid Commun
November 2024
PCFM, LIFM Lab and GD HPPC Lab, School of Chemistry, Sun Yat-sen University, Guangzhou, 510275, P. R. China.
Nanostructures with curved surfaces and chiral-directing residues are highly desirable in the synthesis of asymmetric chemicals, but they remain challenging to synthesize without using unique templates due to the disfavored torsion energy of twisted architectures toward chiral centers. Here, a strategy for the facile fabrication of highly cured capsule-shaped catalysts with chiral interiors by the amplification of molecular chirality via the irreversible cross-linking of 2D asymmetric laminates is presented. The key to the success of these irregular 2D layers is the use of hierarchical assembly of chiral macrocycles, which can exactly regulate the cured nanostructures as well as asymmetric catalysis.
View Article and Find Full Text PDFOrg Lett
November 2024
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Thuggacin A () is a 17-membered-ring-polyketide antibiotic compound with excellent antituberculosis activity. The total synthesis of thuggacin A has not yet been reported so far. Herein, we disclose our efforts toward the convergent total synthesis of thuggacin A.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!