Refernces
10.1039/c4cc02645d
The study presents an efficient synthetic route to produce tosyl-protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs, from biomass-derived furfural. Furfural, a platform chemical derived from agricultural waste like rice straw, is transformed into the piperidone core structure through a series of reactions involving 4-methylbenzenesulfonamide, a Lewis acid catalyst, and a rhodium-catalyzed asymmetric arylation. The aza-Achmatowicz rearrangement and hydrogenation steps further convert the intermediate into the desired piperidone. The synthetic utility of this piperidone is demonstrated by synthesizing a NK1 receptor antagonist. This method is advantageous due to its short synthetic route, high yield, minimal loss of optical purity, and the use of a renewable biomass-derived starting material, addressing sustainability and environmental concerns associated with traditional methods and the disposal of agricultural waste.
10.1021/jo981075c
The research focuses on the synthesis of enantiopure highly substituted trans-8a-hydroxydecahydroisoquinolines, which are significant components of over 500 alkaloids and hold synthetic interest due to their potential biological activity. The study employs a diastereoselective approach involving a sequential intramolecular Diels-Alder (IMDA) reaction and oxanorbornene nucleophilic ring opening, utilizing chiral perhydrobenzoxazines derived from (-)-8-aminomenthol as a chirality inductor. Key chemicals in the process include 2-furaldehyde, (-)-8-((3′-butenyl)amino)menthol, aluminum hydride, pyridinium chlorochromate (PCC), potassium hydroxide, and triethylaluminum, among others. The method allows for the introduction of different substituents at C-1 and C-8 in the final isoquinolines regio- and stereoselectively, leading to the synthesis of a variety of enantiopure isoquinoline derivatives with four stereocenters, three of which are contiguous, and with known absolute configuration. The conclusions of the research highlight the efficiency of this concise and stereocontrolled synthetic method for potentially important biologically active molecules, demonstrating a five-step synthesis from the easily accessible (-)-8-aminomenthol.
10.3987/COM-10-S(E)60
The research focused on the synthesis and characterization of 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids, which were found to be novel substrates for phenylalanine ammonia-lyase (PAL). The purpose of the study was to explore the enzyme's ability to catalyze the conversion of these compounds and to isolate their D- and L-enantiomers. The researchers synthesized the compounds and characterized them using various spectroscopic techniques. They then used recombinant PAL to convert the racemic mixtures into their corresponding acrylates, from which the D-enantiomers were isolated. Conversely, L-enantiomers were prepared by reversing the PAL reaction in the presence of 6 M ammonia at pH 10. The study concluded that these new compounds are good substrates for recombinant PAL and can be resolved into their enantiomers through biocatalysis. The chemicals used in the process included various anilines, furan-2-carbaldehyde, triphenyl-λ5-phosphanilidene acetic acid ethyl ester, and other reagents and solvents for the synthesis and characterization of the novel furanylalanines.