A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123786 | PMC |
http://dx.doi.org/10.3390/molecules26092541 | DOI Listing |
Molecules
February 2025
College of Pharmacy, Dali University, Dali 671000, China.
Efficient and simple syntheses of -dehydroosthol and citrubuntin were achieved in a single step by implementing a protecting-group-free, redox-neutral strategy that utilized readily available starting materials. In this approach, a practical one-pot (domino) Heck/dehydration reaction was carried out utilizing less reactive bromocoumarin, resulting in excellent stereoselectivity and atomic economy. Through the implementation of this new, efficient, and scalable synthesis method, the formal synthesis of a series of novel meroterpenoid natural products was successfully achieved.
View Article and Find Full Text PDFMolecules
February 2025
Department of Chemistry & Biochemistry, University of Missouri-St. Louis, 43 Benton Ct., St. Louis, MO 63121, USA.
Humulones are a family of homolog natural products obtained from the strobiles of humulus lupulus, or hops plants. Structurally, they consist of substituted phloroglucinols with two isoprenyl side chains, a carbonyl group and a quaternary ring carbon substituted with a hydroxyl group. The three most prominent homologs are n-, co- and ad-humulone, containing isobutyl, isopropyl and secbutyl ketone groups, respectively.
View Article and Find Full Text PDFOrg Lett
March 2025
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali 160062, India.
A one-pot process involving cycloaddition of the azaoxyallyl cation with thioamide and a synchronous E1-type elimination of the C2 amino group from the cycloadduct is disclosed, leading to diverse alkylidene-4-thiazolidinones. Amine elimination under acid-free conditions or without quaternization and forging a stereoselective olefin formation were among the interesting reactivity traits revealed through the present work. Conjugated thioamide permitted side-chain branching through a three-component process.
View Article and Find Full Text PDFOrg Lett
March 2025
School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China.
Herein, we describe a highly stereoselective method to access a single olefin isomer from readily available β-hydroxy -hydroxyphthalimide (NHPI) esters. Depending on the configuration of the precursor ( or ), either the or olefin is prepared selectively under Lewis acid-promoted conditions. Without involving radical chemistry, a β-lactone is proposed as the key intermediate in this decarboxylative olefination.
View Article and Find Full Text PDFCommun Chem
March 2025
Freie Universität Berlin, Institute of Chemistry and Biochemistry, Berlin, Germany.
The stereoselective introduction of glycosidic bonds is one of the greatest challenges in carbohydrate chemistry. A key aspect of controlling glycan synthesis is the glycosylation reaction in which the glycosidic linkages are formed. The outcome is governed by a reactive sugar intermediate - the glycosyl cation.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!