Vitamin D and its analogues play a crucial role in promoting the well-being of both humans and animals. However, the current synthesis of this vital class of nutrients heavily relies on chemical transformations, which suffer from low step- and atom-efficiency due to lengthy synthetic pathways. To enhance sustainability in the chemical industry, it is necessary to develop alternative synthetic processes. Herein, we present a photoenzymatic approach for synthesizing 25-hydroxyvitamin D from 7-dehydrocholesterol. In this sequential synthesis, 7-dehydrocholesterol is initially hydroxylated at the C25 C-H bond, resulting in an 85 % conversion to 25-hydroxyl-7-dehydrocholesterol. Subsequently, by employing photo-irradiation using a monochromatic LED ultraviolet light source in a batch reactor and thermal isomerization, 25-hydroxyvitamin D is obtained in satisfactory yield. This photoenzymatic process significantly reduces the need for purification steps and allows for gram-scale synthesis of the target product. Our work offers a selective, efficient, and environmentally friendly method for synthesizing 25-OH-vitamin D, addressing the limitations of current synthetic approaches.
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http://dx.doi.org/10.1002/cssc.202401196 | DOI Listing |
J Am Chem Soc
January 2025
Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Precisely controlling quantum states is relevant in next-generation quantum computing, encryption, and sensing. Chiral organic chromophores host unique light-matter interactions, which allow them to manipulate the quantized circular polarization of photons. Axially chiral organic scaffolds, such as helicenes or twisted acenes, are powerful motifs in chiral light manipulation.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China.
A 6-step gram-scale synthesis of the fungal polyketide (±)-gregatin A is described. The synthetic route features an intermolecular 1,3-dipolar cycloaddition, a Mo-mediated disconnection of the isoxazole skeleton, and an acid-mediated deprotection/enamine hydrolysis and hemiketalization cascade.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Jain University - Ramanagara Campus, Centre for Nano and Material Sciences, Jakkasandra Post Kanakapura Taluk, Ramanagara-562112, Bangalore, 562112, Bangalore, INDIA.
The development of a metallic copper-based catalyst system remains a significant challenge. Herein, we report the synthesis of highly stable, active, and reusable Cu0 catalyst for the carboboration of alkynes using carbon electrophiles and bis(pinacolato)diboron (B2pin2) as chemical feedstocks to afford di- and trisubstituted vinylboronate esters in a regio- and stereoselective manner with appreciable turnover number (TON) of up to 2535 under mild reaction conditions. This three-component coupling reaction works well with a variety of substituted electrophiles and alkynes with broad functional group tolerance.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Tianjin University, Department of Chemistry, #92, Weijin Road, Nankai District, Department of Chemistry, School of Science, Tianjin University, 300072, Tianjin, CHINA.
Electrochemical reductive deuteration of nitriles is a promising strategy for synthesizing deuterated amines with D2O as the deuterated source. However, this reaction suffers from high overpotentials owing to the sluggish D2O dissociation kinetics and high thermodynamic stability of the C≡N triple bond. Here, low-coordinated copper (LC-Cu) is designed to decrease the overpotential for the electrosynthesis of the precursor of Melatonin-d4, 5-methoxytryptamine-d4, by 100 mV with a 68% yield (Faraday efficiency), which is 4 times greater than that of high-coordinated copper (HC-Cu).
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Key Laboratory of Evolution & Marine Biodiversity (Ministry of Education) and Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China.
Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes a cerium-catalyzed cycloaddition of 1-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents.
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