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

31 items
Perspective

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.

Graphical abstract: Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines
Feature Article

The versatility of furfuryl alcohols and furanoxonium ions in synthesis

Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis.

Graphical abstract: The versatility of furfuryl alcohols and furanoxonium ions in synthesis
Review Article

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.

Graphical abstract: Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification
Open Access Communication

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.

Graphical abstract: Isoxazole to oxazole: a mild and unexpected transformation
Communication

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.

Graphical abstract: SmI2–H2O-mediated 5-exo/6-exo lactone radical cyclisation cascades
Open Access Communication

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.

Graphical abstract: New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C
Communication

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.

Graphical abstract: Rhodium(ii)-catalysed tandem aziridination and ring-opening: stereoselective synthesis of functionalised tetrahydrofurans
Open Access Communication

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.

Graphical abstract: A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines
Open Access Communication

[Pd(CN)(X)(PPh3)] palladacycles react with 2,4,6-trifluorophenyl boronic acid to give stable transmetallation products of the type [Pd(CN)(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.

Graphical abstract: [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)]
Open Access Communication

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

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

Graphical abstract: Synthesis and kinetic resolution of N-Boc-2-arylpiperidines
From the themed collection: Celebrating our 2018 prize and award winners
Communication

Synthesis and structure of oxetane containing tripeptide motifs

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

Graphical abstract: Synthesis and structure of oxetane containing tripeptide motifs
Communication

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.

Graphical abstract: Regioselective desymmetrization of diaryltetrahydrofurans via directed ortho-lithiation: an unexpected help from green chemistry
Communication

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.

Graphical abstract: An efficient asymmetric synthesis of (−)-lupinine
Open Access Communication

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.

Graphical abstract: Neocuproine-functionalized silica-coated magnetic nanoparticles for extraction of copper(ii) from aqueous solution
Open Access Communication

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.

Graphical abstract: Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols
Communication

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.

Graphical abstract: Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis
Communication

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.

Graphical abstract: Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation–reductive cleavage sequence
Communication

Efficient syntheses of pillar[6]arene-based hetero[4]rotaxanes using a cooperative capture strategy

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 C3V symmetry in the solid state.

Graphical abstract: Efficient syntheses of pillar[6]arene-based hetero[4]rotaxanes using a cooperative capture strategy
Communication

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.

Graphical abstract: Site-specific cross-linking of collagen peptides by lysyl advanced glycation endproducts
Paper

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.

Graphical abstract: Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins
Paper

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.

Graphical abstract: 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
Paper

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.

Graphical abstract: Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation
Paper

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.

Graphical abstract: Revisiting the sparteine surrogate: development of a resolution route to the (−)-sparteine surrogate
Paper

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.

Graphical abstract: Preparation, anti-trypanosomal activity and localisation of a series of dipeptide-based vinyl sulfones
Paper

Approaches to the total synthesis of chaetochalasin A

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

Graphical abstract: Approaches to the total synthesis of chaetochalasin A
Paper

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.

Graphical abstract: A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues
Open Access Paper

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.

Graphical abstract: Multivalent agents containing 1-substituted 2,3,4-trihydroxyphenyl moieties as novel synthetic polyphenols directed against HIV-1
Paper

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.

Graphical abstract: A total synthesis of (+)-negamycin through isoxazolidine allylation
Paper

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.

Graphical abstract: Antitumour indolequinones: synthesis and activity against human pancreatic cancer cells
Paper

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.

Graphical abstract: Continuous flow chemistry: a discovery tool for new chemical reactivity patterns
Paper

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.

Graphical abstract: Convergent routes to substituted naphthylamides
31 items

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.

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