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This review covers the chemistry and biological aspects of goniothalamin-related styryl
lactones isolated from natural sources. This family of secondary metabolites has been reported to display
diverse uses in folk medicine, but only a limited number of these compounds have been throughly
investigated regarding their biological profile. Herein, we cover the goniothalamin-related styryl
lactones having a C6-C3-C4 framework which appeared in the literature for the first time in the period
2000-2017, and the reports on the synthesis, biological activity and mechanism of action which
were published from 2007-2017.
Herein we describe the high yield synthesis of a highly crystalline cobalt(ii) MOF with a novel zwitterionic ligand made up of 3,3',4,4'-BPTC and 1,4-cyclohexanediamine, obtained in situ during the hydrothermal synthesis. The compound with the molecular formula CHNOCo·2HO has a molecular mass of 965.7783 g mol, a triclinic crystalline system (a = 5.86 Å, b = 9.28 Å, c = 19.92 Å, α = 83.93°, β = 88.01°, γ = 78.59), it is thermally stable up to 300 °C and presents structural stability before and after removing the solvent molecules from its pores. This novel material showed catalytic properties in an electrophilic substitution reaction of indoles and aldehydes allowing the syntheses of bis(indolyl)methanes in high yields under mild reaction conditions and can be reused at least once with the same catalytic activity.
Disclosed
in this Letter is a novel asymmetric addition of alkynyl
nucleophiles to N-alkylpyridinium electrophiles.
The coupling is effected under mild and simple reaction conditions,
affording dihydropyridine products with complete regiochemical and
stereochemical control. In addition to several manipulations of the
dihydropyridine products, the utility of this transformation is demonstrated
through a concise, dearomative, and asymmetric synthesis of (+)-lupinine,
a natural acetylcholine esterase inhibitor.
A one-pot and modular approach to
the synthesis of 2,4(5)-disubstituted
imidazoles was developed based on ketone oxidation, employing catalytic
HBr and DMSO, followed by imidazole condensation with aldehydes. This
methodology afforded twenty-nine disubstituted NH-imidazoles (23%–85% yield). A three-step synthesis of 20
kinase inhibitors was achieved by employing this oxidation–condensation
protocol, followed by bromination and Suzuki coupling in the imidazole
ring to yield trisubstituted NH-imidazoles (23%–69%,
three steps). This approach was also employed in the synthesis of
known inhibitor GSK3037619A.
Disclosed in this communication is a novel asymmetric addition of alkynyl nucleophiles to <i>N</i>-alkyl pyridinium electrophiles. The coupling is effected under mild and simple reaction conditions, affording dihydropyridine products with complete regiochemical and stereochemical control. In addition to several manipulations of the dihyropyridine products, the utility of this transformation is demonstrated through a concise, dearomative, and asymmetric synthesis of (+)-lupinine, a natural acetylcholine esterase inhibitor.
A practical protocol for the first regiodivergent asymmetric addition of aryl and alkenyl organometallic reagents to substituted N‐alkyl pyridinium heterocycles is described. The couplings proceed with high regiochemical and stereochemical selectivities, and provide access to chiral 1,2,3‐ and 1,3,4‐trisubstituted dihydropyridine products, controlled by judicious choice of nitrogen activating agent. To this end, a correlation was found between the parameterized size of the activating group and the C2/C4 regioselectivity in the couplings. The utility of the described chemistry was demonstrated in two concise asymmetric syntheses of (+)‐N‐methylaspidospermidine and (−)‐paroxetine.
This work describes
a method for the difunctionalization of aryl
iodides to generate polysubstituted arenes via Pd catalysis. The reaction
hinges on the unique interplay between norbornene and the metal catalyst
to impart a guided ortho C–H alkylation event
followed by a programmatic ipso borylation to provide
a diverse array of substituted arene products. The utility of this
transformation is demonstrated through the functionalization of the
boronic ester to a variety of valuable functionalities.
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