Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines
This review highlights the H-bond directed diastereoselective epoxidation of allylic alcohols and amines, and contrasts the diastereoselectivity in different cyclic and acyclic systems.
The versatility of furfuryl alcohols and furanoxonium ions in synthesis
Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis.
Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification
Multicomponent assembly processes are key steps in the synthesis of diverse polycyclic heterocycles with a broad array of biological activities.
Isoxazole to oxazole: a mild and unexpected transformation
3-Aryltetrahydrobenzisoxazoles undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this facile transformation was probed and a mechanism proposed.
SmI2–H2O-mediated 5-exo/6-exo lactone radical cyclisation cascades
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.
New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C
A new method for preparing naphthyl amines is described and then used in the syntheses of several benzo[c]phenanthridine natural products.
Rhodium(II)-catalysed tandem aziridination and ring-opening: stereoselective synthesis of functionalised tetrahydrofurans
Rh(II) mediated tandem aziridination and cycloetherification achieves a direct, stereoselective synthesis of the 2-(1-amino-2-hydroxyethyl)tetrahydrofuran motif.
A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines
Rh-catalysed conjugate additions of 2-aminophenyl boronic acid derivatives were exploited in diastereoselective and asymmetric syntheses of tetrahydroquinolines.
[Pd(C∧N)(X)(PPh3)] palladacycles react with 2,4,6-trifluorophenyl boronic acid to give stable transmetallation products of the type [Pd(C∧N)(2,4,6-F3C6H2)(PPh3)]
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.
Synthesis and kinetic resolution of N-Boc-2-arylpiperidines
An efficient kinetic resolution of 2-arylpiperidines was developed using a chiral base.
Synthesis and structure of oxetane containing tripeptide motifs
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.
Regioselective desymmetrization of diaryltetrahydrofurans via directed ortho-lithiation: an unexpected help from green chemistry
ortho-Lithiation/functionalization of diaryltetrahydrofurans proceeds well with t-BuLi both in Et2O and cyclopentyl methyl ether and, remarkably, also in protic eutectic mixtures.
An efficient asymmetric synthesis of (−)-lupinine
The asymmetric synthesis of (−)-lupinine was achieved in 8 steps, 15% overall yield and >99 : 1 dr from commercially available starting materials.
Neocuproine-functionalized silica-coated magnetic nanoparticles for extraction of copper(II) from aqueous solution
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.
Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols
The allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols under palladium catalysis proceeded in a stereoselective fashion with anti-diastereoselectivity.
Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis
Tandem stereospecific rearrangements by [3,3]-sigmatropic shift and N to C aryl migration give tertiary thiols that undergo ring closing metathesis to dihydrothiophenes.
Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation–reductive cleavage sequence
Stereocontrolled access to all the diastereomers of 1,3,5,7-tetraol structural units was developed using a Prins cyclisation–reductive cleavage sequence.
Efficient syntheses of pillararene-based heterorotaxanes using a cooperative capture strategy
While one pillararene, nestling between two cucurbiturils in a heterorotaxane, is conformationally mobile in solution, it adopts the energetically most favourable conformation with local C3V symmetry in the solid state.
Site-specific cross-linking of collagen peptides by lysyl advanced glycation endproducts
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.
Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins
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.
E. coli cells expressing the Baeyer–Villiger monooxygenase ‘MO14’ (ro03437) from Rhodococcus jostii RHA1 catalyse the gram-scale resolution of a bicyclic ketone in a fermentor
(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.
Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation
The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.
Revisiting the sparteine surrogate: development of a resolution route to the (−)-sparteine surrogate
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.
Preparation, anti-trypanosomal activity and localisation of a series of dipeptide-based vinyl sulfones
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.
Approaches to the total synthesis of chaetochalasin A
Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels–Alder reactions.
A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues
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.
Multivalent agents containing 1-substituted 2,3,4-trihydroxyphenyl moieties as novel synthetic polyphenols directed against HIV-1
A series of synthetic polyphenols inspired by the multivalent architecture of naturally-occurring hydrolysable tannins exhibited selective inhibitory activity against HIV-1.
A total synthesis of (+)-negamycin through isoxazolidine allylation
The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate.
Antitumour indolequinones: synthesis and activity against human pancreatic cancer cells
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.
Continuous flow chemistry: a discovery tool for new chemical reactivity patterns
A new reactivity pattern and extended reaction scope has been obtained by transferring a reaction from batch mode to flow.
Convergent routes to substituted naphthylamides
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.
About this collection
We are delighted to present this collection of articles dedicated to Professor Richard Taylor on the occasion of his 65th birthday. This celebration issue published across ChemComm and Organic & Biomolecular Chemistry (OBC) collects some of the latest exciting research in the total synthesis of natural products, the development of new stereoselective transformations, the synthesis of nitrogen and oxygen heterocycles, multicomponent reactions, Pd-mediated chemistry, peptide chemistry and applications of synthesis to materials, supramolecular chemistry and medicinal chemistry. This collection of topics represents Professor Taylor’s broad synthetic interests and is in areas in which he has published key papers during his distinguished career.
Professor Taylor is one of the most popular UK-based organic chemists with numerous friends and acquaintances. This themed collection reflects this, with many contributions from across the UK and all corners of the globe.
Guest Editors: Professors Peter O’Brien, Ray Jones and John Wood.