Synthesis of Immucillins BCX‐1777 and BCX‐4430 from a Common Precursor

A convergent route for the synthesis of BCX-1777 and BCX-4430 from a Boc-protected 2-pyrrolidinone, derived from 2,3,5-tri- O -benzyl- d -ribonolactone, and a dihalogenated pyrrolopyrimidine as the key starting materials is reported. A chemoselective cross-coupling was achieved from the two key starting materials in 79% yield. Luche reduction and...

5h

Ni/g‐C3N4 Photocatalysis: Aerobic Oxidative Coupling Reaction Leading to Amidation of Aldehydes with Amines and C‐N, C‐O, and C‐C Cross‐Coupling Reaction

In the present study, the synthesis of an influential group of organic compounds that are broadly used in pharmaceutical and industrial compounds under completely safe and benign conditions was investigated. Dual nickel/carbon nitride (Ni/g-C3N4) photocatalyst was able to photosynthesize a wide range of amide derivatives under mild, environmentally...

5h

Copper/Iodine‐Catalyzed Hydroxyamination of Alkenyl Keto Oximes Using DMSO as the Oxygen Atom Source and Medium

A new copper/I 2 -catalyzed hydro xyamination of alkenes of unsaturated keto oximes with DMSO as the hydroxy oxygen atom source and medium for assembling 2-(2-hydroxyalkyl)-3,4-dihydro-2 H -pyrrole 1-oxides is described. Mechanistic study experiments suggest that the reaction is terminated by single electron oxidation and subsequent nucleophilic...

1d

Regiodivergent Synthesis of Benzothiazole‐based Isosorbide Imidates by Oxidative N‐Heterocyclic Carbene Catalysis

A novel N-heterocyclic carbene (NHC)-promoted regiodivergent protocol for exo (2-OH) and endo (5-OH) isosorbide (IS) imidates synthesis is described. The disclosed strategy allows the straightforward synthesis of monoimidate-isosorbides (MIIs) endowed with the biologically relevant benzothiazole (BTA) moiety under mild oxidative conditions, starting...

1d

Improved Synthesis Strategy for N‐Methoxy‐1,3‐Oxazinane Nucleic Acids (MOANAs)

Dependence of the hydrolysis rate of a series of N -methoxy-2-phenyl-1,3-oxazinanes on the Hammett substituent constant of the substituent of the phenyl ring was determined, yielding a reaction constant ρ = -1.40 ± 0.05. Based on this information, 4-(benzoyloxy)benzaldehyde was selected as a protecting group for a new (2 R ,3 S )-4-(methoxyamino)butane-1,2,3-triol...

2d

Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are herein described. Highly convergent cascade and one-pot processes afforded the corresponding diarylamines, as in situ formed synthetic intermediates or final products in high overall yields. Special attention was given to the...

2d

Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances

Quinazoline derivatives draw attention from a synthetic and medicinal chemistry point of view, given the wide range of biological activities already described. This class of fused N -heterocyclic compounds has also shown its importance and potential pharmacological application. In this perspective, this minireview covers the contributions reported...

2d

Structurally Forced Ion Binding Affinity: Tetraurea‐Based Macrocycle as a Receptor for Ion Pair

A urea-based complexation site represents a building block customarily used in the design of receptors for anion recognition. Here we report a cyclization driven change of complexation preferences, leading to a urea-based macrocyclic receptor with selectivity for heavier alkali metal cations. Moreover, the thorough 1H and 19F NMR, HRMS and X-ray diffraction...

2d

Light‐Mediated Aminocatalysis: The Dual‐Catalytic Ability Enabling New Enantioselective Route

Over the last few decades, primary and secondary amines have been enormously used to trigger numerous valuable transformations. Likewise, modern-day chemistry has witnessed the potentiality of visible-light photoredox catalysis via single photoelectron transfer reactions. Recently, their synergistic effect has proved to be a crucial synthetic pillar,...

2d

Deep‐sea discovery and detective work: towards solving the hemicalide structural enigma through computational NMR analysis and stereocontrolled synthesis.

The marine natural product hemicalide displays potent anticancer activity. While detailed NMR experiments established the planar carbon skeleton, its full configurational assignment proved enigmatic. This review summarises ongoing synthetic efforts and NMR studies on hemicalide, which have succeeded in reducing the number of possible stereoisomers from...

2d