Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from β-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (β-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7705961 | PMC |
| http://dx.doi.org/10.1021/acs.jnatprod.0c00669 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enzymatic asymmetric synthesis of l-phenylglycine by amino acid dehydrogenases has potential for industrial applications; however, this is hindered by their low catalytic efficiency toward high-concentration substrates. We identified and characterized a novel leucine dehydrogenase (LeuDH) with a high catalytic efficiency for benzoylformic acid via directed metagenomic approaches. Further, we obtained a triple-point mutant LeuDH-EER (D332E/G333E/L334R) with improved stability and catalytic efficiency through the rational design of distal loop 13.
View Article and Find Full Text PDFResearch on transition metals for the multicomponent synthesis of benzo-fused γ-lactams.
RSC Adv
January 2025
Department of Organic Chemistry, Faculty of Chemistry Urmia University Urmia Iran.
Benzo-fused γ-lactams are fundamental in medicinal chemistry, acting as essential elements for various therapeutic agents due to their structural adaptability and capability to enhance biological activity. In their synthesis, transition metals play a pivotal role as catalysts, offering more efficient alternatives to traditional methods by facilitating C-N bond formation through mechanisms like intramolecular coupling. Recent advances have especially spotlighted transition-metal-catalyzed C-H amination reactions for directly converting C(sp)-H to C(sp)-N bonds, streamlining the creation of these compounds.
View Article and Find Full Text PDFImine Synthesis by Engineered d-Amino Acid Oxidase from Porcine Kidney.
ACS Omega
January 2025
Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
Various symmetric and asymmetric imines were synthesized using the novel amine oxidase, obtained as variants of d-amino acid oxidase (pkDAO) from porcine kidney (Y228L/R283G) and (I230A/R283G). Active primary imines produced as intermediates in the oxidation of methylbenzylamine (MBA) derivatives were trapped by aliphatic, aromatic amines and diamines as nucleophiles forming new imines. ()-Fluoro-MBA was the best substrate for symmetric imine synthesis, providing almost stoichiometric conversion (100 mM) and achieving nearly 100% yield.
View Article and Find Full Text PDFRecent Advances in the Design and Application of Asymmetric Carbon-Based Materials.
Small Methods
January 2025
College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang, 050018, P. R. China.
Asymmetric carbon-based materials (ACBMs) have received significant attention in scientific research due to their unique structures and properties. Through the introduction of heterogeneous atoms and the construction of asymmetric ordered/disordered structures, ACBMs are optimized in terms of electrical conductivity, pore structure, and chemical composition and exhibit multiple properties such as hydrophilicity, hydrophobicity, optical characteristics, and magnetic behavior. Here, the recent research progress of ACBMs is reviewed, focusing on the potential of these materials for electrochemical, catalysis, and biomedical applications and their unique advantages over conventional symmetric carbon-based materials.
View Article and Find Full Text PDFMulticomponent Modular Synthesis of Chiral Bicyclic Bridged Compounds via an Alkenylfuran-Based Acylation/Rearrangement/Cyclization Sequence.
Org Lett
January 2025
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
The catalytic asymmetric multicomponent acylation/rearrangement/cyclization of alkenylfurans with acyl oxime esters/arylamines or acyl oxime esters/arylamines/hydroxylamine has been developed. This method employs synergistic photoredox/Brønsted acid catalysis, enabling the efficient and versatile synthesis of multifunctionalized [3.2.
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!