A Diels-Alder reaction leading to 4-nitrophenylcyclohexanones followed by a newly developed base-mediated reductive cyclization of the resulting ketone tethered to the nitrobenzene moiety gives access to the hexahydro-2,6-methano-1-benzazocine ring system present in several biologically interesting natural products such as aspernomine. The scope of the reaction was explored with eight substituted nitrobenzenes, obtaining yields of up to 87%. The highest cytotoxicity was observed in benzazocine , bearing an enone moiety, which was active against eight cancer cell lines.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680033 | PMC |
| http://dx.doi.org/10.1021/acs.joc.2c02205 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses of Bryostatins 1, 7, 9 and 9-N3.
Angew Chem Int Ed Engl
January 2025
Sichuan University, West China School of Pharmacy, Renmin Sout Road, 3rd Section, 17#, 610041, Chengdu, CHINA.
Bryostatins are a family of marine natural products that have garnered significant interests, as evidenced by over 40 clinical trials. However, their extremely low natural abundance has severely limited further research. Despite significant efforts, which have led to the total synthesis of seven bryostatin members by eight independent research groups, these complex molecules present persistent challenges for stereocontrolled, large-scale, and especially divergent synthesis.
View Article and Find Full Text PDFElectrochemical Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide.
Org Lett
January 2025
College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China.
Herein, we present an unprecedented electrochemical reductive cyclizative carboxylation of -vinylphenyl isocyanides with carbon dioxide achieved without the use of metal catalysts. This protocol demonstrates a broad substrate scope and good functional group tolerance, facilitating the rapid assembly of 2-oxoindolin-3-acetic acids in good to high yields with excellent regioselectivity. Furthermore, these structural motifs may have potential applications in formal synthesis of bioactive natural products.
View Article and Find Full Text PDFSubstrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO as a Switching Reagent.
Org Lett
January 2025
College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.
Capturing CO is highly valued in the field of organic synthesis, especially underdeveloped dual-CO conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO.
View Article and Find Full Text PDFCobalt-Catalyzed Enantioselective Reductive Coupling of Imines and Internal Alkynes.
Angew Chem Int Ed Engl
January 2025
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, West Bengal, India.
Chiral allylamines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allylamines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
View Article and Find Full Text PDFFerrocene Catalyzed Radical Cascade Cyclization of Aryl 1,6-Diynes: Access to Cyanoalkylsulfonyl Fluorenes.
Chem Asian J
January 2025
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India.
A ferrocene-catalyzed cyanoalkylsulfonylative radical cascade cyclization of aryl 1,6-diynes using cycloketone oxime esters and DABCO.(SO₂)₂ (DABSO) is reported. The reaction proceeds with notable chemo- and regioselectivity, without requiring additional oxidants or reductants.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!