Olive fruit fly Dacus oleae is a well-known pest infecting the bark of olive fruit, leading to reduction of extracted olive oil properties. Among chemicals proposed for Dacus oleae population control, pheromone 1,7-dioxaspiro(5.5)undecane (DSU), Dacus pheromone, is considered as a promising agent, which is added in several traps. However, all proposed systems manage to sufficiently deliver DSU for only two weeks. Furthermore, an additional problem is the limited available amount of pheromone to use in such systems. To overcome this, in the present study, a novel synthetic procedure of DSU is described, including only five steps. Intermediate products were studied by High Resolution Mass Spectroscopy Electrospray Ionization (HRMS-ESI) (m/z), while the resulting DSU was further characterized by 1H and 13C-NMR. Synthesized DSU was further encapsulated in poly(L-lactic acid) (PLLA) microparticles in three different concentrations; 5, 10 and 20% w/w. Its successful incorporation was studied by FT-IR, XRD and differential scanning calorimeter (DSC) while two procedures, liquid extraction and solid phase microextraction, followed by GC-MS analysis, was used for quantification of pheromone to microparticles. It was found that microparticles loading was over 85% for all three formulations. Its release showed a prolonged profile for microparticles containing 20% w/w DSU, lasting four weeks, while the quantity of DSU released reached 100%. These microparticles could be appropriate to control Dacus oleae population.

Oxazinane rings can undergo isomerization or transformation to 5-membered rings tuned by the anomeric effect.

A novel, conceptually distinct, synthesis of a key precursor to sacubitril, an antihypertensive drug, is presented. The well-demonstrated hetero Diels-Alder addition of in situ generated nitroso alkenes to electron rich enol ethers is engaged to establish the required functionalities with controllable relative stereochemistry. An asymmetric variant of the enol ether enables the access to the target molecule in enantiopure form.

A library of novel 2-substituted derivatives of the antibiotic natural product pentenomycin I is presented. The new collection of analogues is divided in two main classes, 2-alkynyl- and 2-aryl- derivatives, which are accessed by the appropriate type of palladium-catalyzed cross-coupling reaction of the 2-iodo-protected pentenomycin I with suitable nucleophiles. The new derivatives were tested for their activity against certain types of bacteria and one of them, compound 8h, was found to exhibit significant inhibitory activity against several Gram-positive bacteria but also displayed cytotoxic activity against eukaryotic cell lines.

An eco-friendly, high-yielding, and transition-metal-free synthesis of 2-[(2,4-dimethylphenyl)thio]aniline precursor to vortioxetine is reported. Vortioxetine, a multi-modal acting drug with high affinity for a range of serotonergic targets, is used for the treatment of major depressive disorder (MDD). The synthesis – applicable in multi-gram scale – involves the reaction of bis(2,4-dimethyl)iodonium bromide with commercial 2-aminophenyl disulfide, whereas its reaction with 2-aminothiophenol afforded the same product but in low to moderate yields. This method works equally well in deep eutectic solvents (DESs), based on choline chloride (ChCl).