Themed collection In Celebration of Richard Taylor’s 65th Birthday

This review highlights the H-bond directed diastereoselective epoxidation of allylic alcohols and amines, and contrasts the diastereoselectivity in different cyclic and acyclic systems.

Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis.

Multicomponent assembly processes are key steps in the synthesis of diverse polycyclic heterocycles with a broad array of biological activities.

3-Aryltetrahydrobenzisoxazoles undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this facile transformation was probed and a mechanism proposed.

5-exo/6-exo lactone radical cyclisation cascades deliver carbo[5.4.0]bicycles in a diastereoselective, one-pot process using SmI₂ in the presence of H₂O.

A new method for preparing naphthyl amines is described and then used in the syntheses of several benzo[c]phenanthridine natural products.

Rh(II) mediated tandem aziridination and cycloetherification achieves a direct, stereoselective synthesis of the 2-(1-amino-2-hydroxyethyl)tetrahydrofuran motif.

Rh-catalysed conjugate additions of 2-aminophenyl boronic acid derivatives were exploited in diastereoselective and asymmetric syntheses of tetrahydroquinolines.

Evidence for a direct transmetallation between a palladacycle (containing acetate and imidate pseudohalides) with 2,4,6-trifluorophenyl boronic acid is presented in this paper.

An efficient kinetic resolution of 2-arylpiperidines was developed using a chiral base.

A new class of peptidomimetic is made in which the central amide CO bond of a tripeptide is replaced by an oxetane ring. Structural insights are provided by X-ray diffraction and molecular dynamics simulations.

ortho-Lithiation/functionalization of diaryltetrahydrofurans proceeds well with t-BuLi both in Et₂O and cyclopentyl methyl ether and, remarkably, also in protic eutectic mixtures.

The asymmetric synthesis of (−)-lupinine was achieved in 8 steps, 15% overall yield and >99 : 1 dr from commercially available starting materials.

Neocuproine has been covalently bound to silica-coated maghemite (γ-Fe₂O₃) magnetic nanoparticles (MNPs) by a phenyl ether linkage. The resulting MNPs are able to remove Cu(II) from 12 ppm aqueous solution with an extraction efficiency of up to 99% at pH 2.

The allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols under palladium catalysis proceeded in a stereoselective fashion with anti-diastereoselectivity.

Tandem stereospecific rearrangements by [3,3]-sigmatropic shift and N to C aryl migration give tertiary thiols that undergo ring closing metathesis to dihydrothiophenes.

Stereocontrolled access to all the diastereomers of 1,3,5,7-tetraol structural units was developed using a Prins cyclisation–reductive cleavage sequence.

While one pillar[6]arene, nestling between two cucurbit[6]urils in a hetero[4]rotaxane, is conformationally mobile in solution, it adopts the energetically most favourable conformation with local C_3V symmetry in the solid state.

Cross-linking lysyl AGEs were synthesised and incorporated into two types of collagen peptides and now enable detailed analysis of the effects these cross-links have on biological systems.

The trimeric C-type lectin MGL is involved in activating immune defence and virus uptake, thus becoming a target for inhibitor design. A tetravalent cluster with α-S-GalNAc proved to be effective in the nM range.

(1S,5R)-2-Oxalactone of >99% ee and (1S,5R)-ketone of 96% ee are produced after approximately 14 h at a temperature of 16 °C.

The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.

A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (−)-O,O′-di-p-toluoyl-L-tartaric acid is reported. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.

An improved, Weinreb amide-based, synthesis of anti-trypanosomal lysine-containing vinyl sulfones is described incorporating, as a feature, diversity at the ε-lysine amino group.

Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels–Alder reactions.

A palladium-catalyzed C–S coupling reaction has been used as a key step for the introduction of S-functionality at the C-5 position of the cytosine and uracil nucleosides and their analogues.

A series of synthetic polyphenols inspired by the multivalent architecture of naturally-occurring hydrolysable tannins exhibited selective inhibitory activity against HIV-1.

The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate.

An important determinant of the growth inhibitory activity of indolequinones against pancreatic cancer cells is substitution on the 2-position with 2-unsubstituted derivatives being markedly more potent.

A new reactivity pattern and extended reaction scope has been obtained by transferring a reaction from batch mode to flow.

Substituted 1- and 2-naphthylamides can be obtained by the radical addition–cyclisation of amido-containing phenacyl xanthates to vinyl pivalate followed by acid catalysed aromatisation.