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Density Functional Theory Rationalization of the Mechanism, Selectivity, and Role of Substituents in Au(I)-Catalyzed Synthesis of Pyrazolines and Dihydropyridines.
J Org Chem
December 2024
College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, P. R. China.
Article Synopsis
- - A study investigated how gold catalysts affect the synthesis of pyrazolines and dihydropyridines from imines and methyl phenylpropiolate, focusing on three different imines with unique substituents.
- - The research found that the type of nitrogen substituent influences the reaction path: NHCOMe leads to outward ring opening and pyrazoline products, while aromatic substituents prompt inward ring opening and dihydropyridine products.
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A relay ring-closing metathesis/Diels-Alder approach to sugar-derived pluramycin-hybrids.
Org Biomol Chem
August 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
Herein, we present a general approach for synthesizing pluramycin hybrids, which are analogous to the pluramycinone carbocyclic skeleton. This method involves a sequence of relay ring-closing enyne metathesis, Diels-Alder and oxidative aromatization reactions to synthesize pluramycinone-sugar hybrids. As part of our ongoing research, we have successfully synthesized two pluramycin hybrid analogues by carefully monitoring the late-stage oxidative aromatization steps, which depend on the stereo-orientation of the Diels-Alder cycloadduct at the C-4 center.
View Article and Find Full Text PDFPhotochemical Divergent Ring-Closing Metathesis of 1,7-Enynes: Efficient Synthesis of Spirocyclic Quinolin-2-ones.
Org Lett
August 2024
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, People's Republic of China.
A photocatalytic method for the ring-closing 1,7-enyne metathesis using the α-amino radical as an alkene deconstruction auxiliary is present. Preliminary mechanistic studies suggest that intramolecular 1,5-hydrogen atom transfer is the key to the generation and β-scission of the α-amino radical, while the dearomatization of arenes and ring opening of cyclopropanes are the key to construct spirocyclic quinolin-2-ones. This approach highlights the potential of ring-closing 1,7-enyne metathesis, providing a green, efficient, and step-economical way for the synthesis of spirocyclic quinolin-2-ones.
View Article and Find Full Text PDFAsymmetric Total Synthesis of 4-Hydroxy-8--methyltetrangomycin, 4-Hydroxytetrangomycin, and 4-Keto-8--methyltetrangomycin.
J Org Chem
August 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Herein, we report the first asymmetric total synthesis of 4-hydroxy-8--methyltetrangomycin (), 4-hydroxytetrangomycin (), and 4-keto-8--methyltetrangomycin (), angucyclinones featuring a highly oxidized nonaromatic A ring. A sequential enyne metathesis/Diels-Alder approach was utilized successfully to construct the tetracyclic skeleton of the angucyclinones. Late-stage acetonide deprotection challenges were overcome by A ring functional group manipulation, yielding a dihydroxy intermediate prior to the benzylic photo-oxidation, facilitating the total syntheses of angucyclinones -.
View Article and Find Full Text PDFChiral Acetal-Based Stereo-Controlled Degradable Polymer Synthesis.
Chemistry
September 2024
Department of Chemistry, Chungbuk National University, 1 Chungdae-ro, Seowon-gu, Cheongju, 28644, Republic of Korea.
The precise synthesis of chiral polymers remains a significant challenge in polymer chemistry, particularly for applications in advanced biomedical and electronic materials. The development of degradable polymers is important for eco-friendly and advanced materials. Here, we introduce a stereo-controlled degradable polymer via cascade enyne metathesis polymerization and enantioselective acetal synthesis through Pd-catalyzed asymmetric hydroamination.
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