Deoxygenative Divergent Synthesis: En Route to Quinic Acid Chirons.

Org Lett

Faculty of Engineering and Natural Sciences, Tampere University, Korkeakoulunkatu 8, 33101 Tampere, Finland.

Published: November 2020

The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.0c02995DOI Listing

Publication Analysis

Top Keywords

quinic acid
8
deoxygenative divergent
4
divergent synthesis
4
synthesis route
4
route quinic
4
acid chirons
4
chirons installation
4
installation vicinal
4
vicinal mesylate
4
mesylate silyl
4

Similar Publications

Background: Fruit quality traits, including taste, flavor, texture, and shelf-life, have emerged as important breeding priorities in blueberry (Vaccinium corymbosum). Organic acids and sugars play crucial roles in the perception of blueberry taste/flavor, where low and high consumer liking are correlated with high organic acids and high sugars, respectively. Blueberry texture and appearance are also critical for shelf-life quality and consumers' willingness-to-pay.

View Article and Find Full Text PDF

The Italian Carciofo di Paestum () PGI, an artichoke variety from the Campania region, was investigated for its potential to reuse by-products for food supplements. EtOH:HO 50:50 and 75:25 extracts of its leaves were analyzed for phenolic and flavonoid content and antioxidant activity (TEAC: 1.90 and 1.

View Article and Find Full Text PDF

Stability of Selected Phenolic Acids Under Simulated and Real Extraction Conditions from Plants.

Molecules

December 2024

Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Skłodowska University in Lublin, Pl. Maria Curie-Skłodowska 3, 20-031 Lublin, Poland.

Currently, there is a significant demand for natural biologically active compounds. Emphasis is placed on improving the quality and safety of processed natural products, which is understandable in light of the frequently observed instability of natural compounds and their degradation, among others, to compounds of unknown biological activity. In this paper, the influence of typical conditions of currently used assisted extraction techniques on the stability of 5-O-caffeoylquinic acid and 1,3-di-O-caffeoylquinic acid during their simulated and real extraction from plants was investigated.

View Article and Find Full Text PDF

To gain a deeper understanding of the mechanisms by which cushioning packaging preserves the quality of Chinese olive fruits during cold chain transportation and extends their shelf life, this study simulated cold chain conditions and investigated the effects of cushioning packaging on the physiology, antioxidant capacity, and secondary metabolites of fruits during a 20-day shelf life. The results indicated that the decay rate in cushioning-packaging-treated fruit was 75% lower than that in the unbuffered packaging fruit at day 20 of shelf life. Simultaneously, cushioning packaging treatment mitigated the damage severity of the cell membrane structure and kept the cell membrane permeability at a low level, which was 15.

View Article and Find Full Text PDF

Dissecting Interactions of and to Shape Kiwifruit Wine Flavor.

Foods

December 2024

Key Laboratory of the Evaluation and Monitoring of Southwest Land Resources (Ministry of Education), Sichuan Normal University, Chengdu 610101, China.

Mixed fermentation with and has been shown to enhance wine aroma, yet the underlying mechanisms remain unclear. Monoculture of , monoculture of , and mixed culture of and were conducted, and the study analyzed and compared the biomass, flavor profile, and transcriptome responses of the three groups. Both yeast species exhibited growth inhibition in mixed culture, especially .

View Article and Find Full Text PDF

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!