Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a NaCO/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.1c01569DOI Listing

Publication Analysis

Top Keywords

synthesis cyclopentenones
8
acrylic acids
8
acids formaldehyde
8
formaldehyde malonates
8
cyclopentenones rhodium-catalyzed
4
rhodium-catalyzed c-h
4
c-h annulation
4
annulation acrylic
4
malonates efficient
4
efficient rhodium-catalyzed
4

Similar Publications

The global increase in hyperuricemia, a pathological condition characterized by elevated serum urate concentrations, emphasizes the importance of appropriate management of uric acid homeostasis in the body. Enhancing renal urate excretion is clinically relevant to achieve serum urate-lowering, and the functional inhibition of urate transporter 1 (URAT1), a renal urate transporter involved in the reabsorption of urate, has been recognized as a promising strategy. In this context, natural substances, including food ingredients with URAT1-inhibitory activity, have garnered significant interest.

View Article and Find Full Text PDF

Neuroprostanes (NeuroPs) are bioactive oxylipins formed in vivo from docosahexaenoic acid (DHA), the main polyunsaturated fatty acid of the human brain, by a nonenzymatic auto-oxidative process as mixtures of regio- and diastereoisomers. Thus, synthetic material is necessary to unlock their potential as oxidative stress biomarkers as well as to investigate the biological properties of individual NeuroP molecules. Despite recent advances in the field, cyclopentenone-type NeuroPs have received limited attention.

View Article and Find Full Text PDF

We describe an intramolecular double Michael addition reaction using 1,3-cyclopentanediones with a Michael acceptor at the C3' position of the C2 side chain through the formal umpolung of the 1,3-cyclopentanedione moiety. Silylation of the reactants generates 1,4-bis(silyloxy)cyclopentadienes, a silyloxy-substituted carbon which attacks the Michael acceptor to afford bicyclic scaffolds. Appropriate selection of the Michael acceptor induces further cyclization toward the activated cyclopentenone moiety to form a cyclobutane ring, affording cyclobuta[]pentalenes.

View Article and Find Full Text PDF

Multisubstituted cyclopentenones and 1,4-diketones are valuable chemicals for synthesizing biologically relevant compounds. We established the Rh(III)-catalyzed divergent synthesis of multisubstituted cyclopentenones and 1,4-diketones from quinoline-8-carbaldehydes and cyclopropanols. Switchable product selectivity was achieved using different cyclopropyl alcohols under the optimized reaction conditions.

View Article and Find Full Text PDF

GPR44-Dependent Regulation of the Selenoproteome by eIF4a3 in Murine Acute Myeloid Leukemia-Initiating Stem Cells.

Biol Trace Elem Res

June 2025

Department of Veterinary and Biomedical Sciences, Center for Molecular Immunology and Infectious Disease and Center for Molecular Toxicology and Carcinogenesis, The Pennsylvania State University, University Park, PA, 16802, USA.

Acute myeloid leukemia (AML) remains an aggressive hematologic malignancy, with leukemia-initiating stem cells (LICs) playing a critical role in disease progression and therapeutic resistance. In this study, we investigated the role of GPR44, a G-protein coupled receptor of arachidonic acid-derived prostaglandin D (PGD) and its cyclopentenone prostaglandins (CyPGs) metabolites, Δ-PGJ and 15d-PGJ, in regulating selenium metabolism and selenoprotein expression in AML LICs. Transplantation of Gpr44 LICs into donor mice led to aggressive leukemogenesis.

View Article and Find Full Text PDF