The Prins reaction is a very convenient synthetic platform for the preparation of oxygen-containing heterocyclic compounds, especially tetrahydropyrans and tetrahydrofurans. While this reaction has been extensively used by synthetic chemists since its discovery, the last years have witnessed impressive improvements in its performance and scope and especially in the development of new catalytic and enantioselective versions. This mini-review presents these recent advances through selected representative examples.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9476534 | PMC |
| http://dx.doi.org/10.1021/acsomega.2c04765 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization.
Org Biomol Chem
January 2025
Univ Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.
A straightforward and highly diastereoselective synthesis of -4-hydroxypiperidines is presented. This method allows access to C2 and C4 substituted piperidines, bearing a tetrasubstituted carbon stereocenter at C4. -Disubstituted homoallylic amines and ketoaldehydes as carbonyl partners have been rarely used in aza-Prins cyclizations, expanding the scope of this reaction.
View Article and Find Full Text PDFTotal Synthesis of Eribulin, a Macrocyclic Ketone Analogue of Halichondrin B, via Prins Macrocyclization.
Org Lett
December 2024
Eisai Inc. G2D2, 35 Cambridgepark Drive, Cambridge, Massachusetts 02140, United States.
An entirely chromium-free synthesis of eribulin, a fully synthetic macrocyclic ketone analogue of the marine natural product halichondrin B, was achieved through iterative sulfone fragment couplings followed by an intramolecular Prins reaction involving a C.26 homoallenyl alcohol and a C.27 aldehyde acetal.
View Article and Find Full Text PDFExpression, Purification, and Characterisation of Recombinant Alginate Lyase ( AL2) for the Bioconversion of Alginate into Alginate Oligosaccharides.
Molecules
November 2024
Enzyme Science Programme (ESP), Department of Biochemistry, Microbiology and Bioinformatics, Rhodes University, Makhanda 6140, South Africa.
Alginate, a polysaccharide found in brown seaweeds, has regularly gained attention for its potential use as a source of bioactive compounds. However, it is structurally complex with a high molecular weight, limiting its application. Alginate oligosaccharides (AOS) are small, soluble fragments, making them more bioavailable.
View Article and Find Full Text PDFExploring Interrupted Nazarov Cyclizations Using Tethered Sulfonamide Nucleophiles: Insights into Capture Pathways.
European J Org Chem
November 2024
Department of Chemistry, University of Rochester, Rochester, NY 14627.
This manuscript describes a study of diverse reaction outcomes that stem from the ionization of -alkynyl-Prins adducts. Experimental results have demonstrated unexpected behavior in the nitrogen-containing systems compared to the analogous oxygen derivatives derived from -Prins/-Nazarov sequences. In-depth experimental studies and computational analysis revealed an intricate mechanism involving competing -Nazarov and -Nazarov pathways.
View Article and Find Full Text PDFBioinspired Total Synthesis of Natural Products.
Acc Chem Res
December 2024
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Article Synopsis
- The text discusses the challenges in total synthesis of natural products, focusing on improving efficiency and allowing for diverse syntheses.
- It highlights the use of bioinspired synthesis, especially late-stage skeletal diversification, as an effective strategy to achieve these goals.
- The authors summarize their research efforts, including key methods that mimic natural biosynthetic reactions to create complex molecules efficiently, showcasing successful syntheses of various natural products.
Want 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!