Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes
status: published
Biomimetic total syntheses of amorfrutins A, B, (S)-D and (R)-D and formal synthesis of amorfrutin C
Bibenzyl natural products, such as the amorfrutins, contain a heavily substituted aromatic core and display a diverse range of biological activities (anti-tumor, anti-diabetic, antimicrobial, and antibiotic). In this study, we report unified syntheses of amorfrutin A to D either through total or formal synthesis by employing a dual biomimetic strat...
Solvent-free N-Boc deprotection by ex situ generation of hydrogen chloride gas
An efficient, scalable and sustainable method for the quantitative deprotection of the tert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate the ex situ generation of hydrogen chloride gas from sodium chloride and sulfuric acid in a t...
Exploration of human xylosyltransferase for chemoenzymatic synthesis of proteoglycan linkage region
Proteoglycans (PGs) play important roles in many biological processes including tumor progression, cell adhesion, and regulation of growth factor activities. With glycosaminoglycan chains attached to the core proteins in nature, PGs are highly challenging synthetic targets due to the difficulties in integrating the sulfated glycans with the peptide...
Starch hydrolysis during mashing: A study of the activity and thermal inactivation kinetics of barley malt alpha-amylase...
Hydrolysis of starch is key in several industrial processes, including brewing. Here, the activity and inactivation kinetics of amylases throughout barley malt mashing are investigated, as a prerequisite for rational optimisation of this process. Varietal differences were observed in the activity of α- and β-amylases as a function of temperature fo...
Photochemical and Electrochemical Strategies towards Benzylic C-H Functionalization: A Recent Update
status: published
Combinatorial effects of coral addition and plasma treatment on the properties of chitosan/polyethylene oxide nanofibers...
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Given the complex calcified nature of the fibrous bone tissue, a combinatorial approach merging specific topographical/biochemical cues was adopted to design bone tissue-engineered scaffolds. Coral having a Ca-enriched structure was added to electrospun chitosan (CS)/polyethylene oxide (PEO) nanofibers that were subjected to plasma surface modifica...
Biomimetic syntheses of amorfrutin C and C-5 substituted amorfrutin analogues
Amorfrutin C, a C-5 prenyl amorfrutin, its allyl analog and an amorfrutin C-5 aldehyde have been synthesized using a biomimetic strategy from non-aromatic precursors. In this approach, a dioxinone derived β,δ-diketo ester underwent a decarboxylative Pd(0) catalyzed prenyl migration to give a β,δ-diketo dioxinone, which readily aromatized giving the...
Regioselective electrochemical cyclobutanol ring expansion to 1-tetralones
A mild electrochemical method for the regioselective preparation of 1‐tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic‐ and heteroaromatic‐fused 1‐tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy ra...
Biomimetic syntheses of analogs of hongoquercin A and B by late-stage derivatization
The hongoquercins are tetracyclic meroterpenoid natural products with the trans–transoid decalin-dihydrobenzopyran ring system, which display a range of different bioactivities. In this study, the syntheses of a range of hongoquercins using gold-catalyzed enyne cyclization reactions and further derivatization are described. The parent enyne resorcy...
