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10 of the best: Supramolecular chemistry in OBC

25 Jun 2012

This week we’re going supramolecular as we celebrate OBC’s 10th anniversary! Below is a selection of 10 of our most highly cited articles in the area of supramolecular chemistry. Every single one will be free to access for you to enjoy for the next week.

Multivalency in supramolecular chemistry and nanofabrication
Alart Mulder, Jurriaan Huskens and David N. Reinhoudt
DOI: 10.1039/B413971B

New directions in supramolecular transition metal catalysis
Matthew J. Wilkinson, Piet W. N. M. van Leeuwen and Joost N. H. Reek
DOI: 10.1039/B503407H

Nucleation–elongation: a mechanism for cooperative supramolecular polymerization
Dahui Zhao and Jeffrey S. Moore
DOI: 10.1039/B308788C

Mass spectrometric studies of non-covalent compounds: why supramolecular chemistry in the gas phase?
Bilge Baytekin, H. Tarik Baytekin and Christoph A. Schalley
DOI: 10.1039/B604265A

Artificial photosynthetic systems: assemblies of slipped cofacial porphyrins and phthalocyanines showing strong electronic coupling
Akiharu Satake and Yoshiaki Kobuke
DOI: 10.1039/B703405A

Bright molecules with sense, logic, numeracy and utility
A. Prasanna de Silva, Thomas P. Vance, Matthew E. S. West and Glenn D. Wright
DOI: 10.1039/B802963F

Tetrakis(imidazolium) macrocyclic receptors for anion binding
Wallace W. H. Wong, Matthew S. Vickers, Andrew R. Cowley, Rowena L. Paul and Paul D. Beer
DOI: 10.1039/B510068B

Anion-templated assembly of [2]rotaxanes
Mark R. Sambrook, Paul D. Beer, Michael D. Lankshear, R. Frederick Ludlow and James A. Wisner
DOI: 10.1039/B518178J

A versatile template for the formation of [2]pseudorotaxanes. 1,2-Bis(pyridinium)ethane axles and 24-crown-8 ether wheels
Stephen J. Loeb, Jorge Tiburcio, Sarah J. Vella and James A. Wisner
DOI: 10.1039/B514528G

Interlocked host rotaxane and catenane structures for sensing charged guest species via optical and electrochemical methodologies
Michał J. Chmielewski , Jason J. Davis and Paul D. Beer
DOI: 10.1039/B818351A

Take a look here for some of our top cited work, including more 10 of the bests:

bioorganic, catalysis, medicinal chemistry, natural products.

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OBC issue 27, featuring continuous-flow synthesis and core-modified porphyrins

21 Jun 2012

The front cover (right) of this issue of Organic & Biomolecular Chemistry features the work Takashi Takahashi and colleagues at Tokyo Institute of Technology. Takahashi et al. present a two-stage continuous-flow synthesis of activated vitamin D₃, the first application of a micro-flow system to this synthesis. The authors claim that the synthesis should be easy to scale up and that it required no purification of intermediates or high dilution conditions, and so reducing wastage.

Continuous-flow synthesis of activated vitamin D₃ and its analogues
Shinichiro Fuse, Yuto Mifune, Nobutake Tanabe and Takashi Takahashi

The inside cover (left) highlights work by Chihiro Maeda and Naoki Yoshioka, Keio University, on the synthesis of peripherally ethynylated carbazole-based core-modified porphyrins. Maeda and Keio make use of a series of metal-catalyzed coupling and annulation reactions to produce the porphyrins whose π-conjugated networks are shown to effectively delocalise over the entire macrocycle.

Peripherally ethynylated carbazole-based core-modified porphyrins
Chihiro Maeda and Naoki Yoshioka

As always these cover articles are free to access for 6 weeks.

Also in this issue is this HOT communication:

First total synthesis of the biscarbazole alkaloid oxydimurrayafoline
Carsten Börger, Micha P. Krahl, Margit Gruner, Olga Kataeva and Hans-Joachim Knölker

And, the perspective ‘Strategies for the enantioselective synthesis of spirooxindoles’

Find the complete issue HERE….

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HOT: First total synthesis of the biscarbazole alkaloid oxydimurrayafoline

19 Jun 2012

Biscarbazoles are a class of carbazole alkaloids in which two carbazole moieties are connected by different linkages. Oxydimurrayafoline is a special biscarbazole connecting two carbazole units via a benzylic ether linkage at the 3-position.

In this HOT Communication, Hans-Joachim Knölker and co-workers from Technische Universität Dresden, report the first total synthesis of oxydimurrayafoline via nucleophilic substitution at the benzylic position at the C-3 position of the carbazole framework.

Knölker et al. use a palladium catalysis approach to produce the key intermediate mukonine in 2 steps before going on to make oxydimurrayafoline in a total of 6 steps with an overall yield of 43%.

This Communication will be FREE to access for the next 4 weeks, so have a look at the details of the study today.

First total synthesis of the biscarbazole alkaloid oxydimurrayafoline
Carsten Börger, Micha P. Krahl, Margit Gruner, Olga Kataeva and Hans-Joachim Knölker
DOI: 10.1039/C2OB25842K

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10 of the best: Natural Products in Organic & Biomolecular Chemistry

18 Jun 2012

In the latest blog of our series celebrating OBC’s 10th anniversary we bring you a selection of 10 of our most highly cited articles in the area of natural products. Every single one will be free to access for you to enjoy for the next week.

Triggering cryptic natural product biosynthesis in microorganisms
Kirstin Scherlach and Christian Hertweck
DOI: 10.1039/B821578B

Chemistry and biology of wortmannin
Peter Wipf and Robert J. Halter
DOI: 10.1039/B504418A

[3 + 3] Cycloadditions and related strategies in alkaloid natural product synthesis
Joseph P. A. Harrity and Olivier Provoost
DOI: 10.1039/B502349C

Discovery and optimization of non-steroidal FXR agonists from natural product-like libraries
K. C. Nicolaou, Ronald M. Evans, A. J. Roecker, Robert Hughes, Michael Downes and Jeffery A. Pfefferkorn
DOI: 10.1039/B300525A

Golden opportunities in natural product synthesis: first total synthesis of (−)-isocyclocapitelline and (−)-isochrysotricine by gold-catalyzed allene cycloisomerization
Frank Volz and Norbert Krause
DOI: 10.1039/B703995F

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition
Elin Abraham, E. Anne Brock, José I. Candela-Lena, Stephen G. Davies, Matthew Georgiou, Rebecca L. Nicholson, James H. Perkins, Paul M. Roberts, Angela J. Russell, Elena M. Sánchez-Fernández, Philip M. Scott, Andrew D. Smith and James E. Thomson
DOI: 10.1039/B801671B

Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
Dimitrios E. Lizos and John A. Murphy
DOI: 10.1039/B208114H

Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides
Panumart Thongyoo, Núria Roqué-Rosell, Robin J. Leatherbarrow and Edward W. Tate
DOI: 10.1039/B801667D

Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
Martin G. Banwell, Alison J. Edwards, Katrina A. Jolliffe, Jason A. Smith, Ernest Hamel and Pascal Verdier-Pinard
DOI: 10.1039/B209992F

Enantioselective synthesis of (+)(R)- and (−)(S)-nicotine based on Ir-catalysed allylic amination
Carolin Welter, Rosa M. Moreno, Stephane Streiff and Günter Helmchen
DOI: 10.1039/B508634E

Missed our other 10th anniversary posts? Take a look here for some of our top cited work, including 10 of the best catalysis articles and 10 of the best medicinal chemistry articles.

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A glimpse of OBC issue 26 and its metallic organophosphates and rubesanolide covers

13 Jun 2012

The latest issue of OBC is now available to access, and here’s a quick peek…

Steaming its way on to the front cover is this image (right) from Alejandro Parra & José Alemán et al. Their perspective gives the reader a general overview of some of the most relevant topics in the applications of chiral metallic organophosphates, and includes a selection of the most outstanding uses of these catalysts.

Metallic organophosphates as catalysts in asymmetric synthesis: a return journey
Alejandro Parra, Silvia Reboredo, Ana M. Martín Castro and José Alemán
Org. Biomol. Chem., 2012, 10, 5001–5020

And coming into bloom on the inside cover is this image (left) highlighting the work Hongjie Zhang et al. describing the isolation and structure elucidation of 3 novel abietane diterpenoids, rubesanolides C–E (1–3) from the leaves of the medicinal plant Isodon rubescens

Rubesanolides C–E: abietane diterpenoids isolated from Isodon rubescens and evaluation of their anti-biofilm activity
Juan Zou, Lutai Pan, Qiji Li, Jianxin Pu, Ping Yao, Min Zhu, Jeffrey A. Banas, Hongjie Zhang and Handong Sun
Org. Biomol. Chem., 2012, 10, 5039–5044

Read both for FREE for the next 6 weeks!

As well as many excellent papers, there is also this perspective by Ramakrishna Edupuganti and Franklin A. Davis on the synthesis and applications of masked oxo-sulfinamides in asymmetric synthesis.

Find the complete OBC issue 26 here…

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Outstanding organocatalysis: An article collection

13 Jun 2012

Catalysts are key to some of the most important reactions on the planet; a world without the Haber process or catalysts to crack crude oil is difficult to imagine. Not to mention the enzymatic reactions that are crucial to all life on earth.

Organocatalysts are an important class of catalyst and consist of carbon-based molecules often functionalised with oxygen, sulfur, nitrogen or phosphorus. They have shown promise in a range of reactions including hydrogenation, Diels-Alder, Michael and Mannich reactions, and are of particular interest in asymmetric reactions.

To help keep you up-to-date with the latest in cutting-edge organocatalytic research we have made the following articles free to access until the 9th July. After reading all these there will be little you won’t know about the exciting world of organocatalysis!

Click here for the full list of free articles

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10 of the best: medicinal chemistry in Organic & Biomolecular Chemistry

12 Jun 2012

Continuing our blog series celebrating OBC’s 10th anniversary we bring you a selection of 10 of our most highly cited articles in the area of medicinal chemistry. Every single one will be free to access for you to enjoy for the next week.

Analysis of the reactions used for the preparation of drug candidate molecules
John S. Carey, David Laffan, Colin Thomson and Mike T. Williams
DOI: 10.1039/B602413K

A hitchhiker’s guide to G-quadruplex ligands
David Monchaud and Marie-Paule Teulade-Fichou
DOI: 10.1039/B714772B

HIV-1 protease: mechanism and drug discovery
Ashraf Brik and Chi-Huey Wong
DOI: 10.1039/B208248A

Cell-penetrating peptides as delivery vehicles for biology and medicine
Kelly M. Stewart, Kristin L. Horton and Shana O. Kelley
DOI: 10.1039/B719950C

Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug
Young Jin Jeon, Soo-Young Kim, Young Ho Ko, Shigeru Sakamoto, Kentaro Yamaguchi and Kimoon Kim
DOI: 10.1039/B504487A

Synthesis and evaluation of analogues of 10H-indolo[3,2-b]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase
Bérangère Guyen, Christoph M. Schultes, Pascale Hazel, John Mann and Stephen Neidle
DOI: 10.1039/B316055F

Mechanism and structure–reactivity relationships for aromatic hydroxylation by cytochrome P450
Christine M. Bathelt, Lars Ridder, Adrian J. Mulholland and Jeremy N. Harvey
DOI: 10.1039/B410729B

The merger of natural product synthesis and medicinal chemistry: on the chemistry and chemical biology of epothilones
Karl-Heinz Altmann
DOI: 10.1039/B405839A

Two-stage enzyme mediated drug release from LMWG hydrogels
Kjeld J. C. van Bommel, Marc C. A. Stuart, Ben L. Feringa and Jan van Esch
DOI: 10.1039/B507157G

Designer aminoglycosides: the race to develop improved antibiotics and compounds for the treatment of human genetic diseases
Mariana Hainrichson, Igor Nudelman and Timor Baasov
DOI: 10.1039/B712690P

Missed our other 10th anniversary posts? Take a look here for some of our top cited work.

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OBC issue 25 now online: featuring Yamada–Otani condensation & organocatalytic dendrimers

07 Jun 2012

Welcome, dear reader, to issue 25 of OBC!

The front cover of this week’s issue highlights the work of Rich G. Carter, Oregon State University, and colleagues. In this paper Carter et al. present the development of a proline sulphonamide-catalysed method that facilitates the annulation of α-aryl, α-alkyl-disubstituted aldehydes with acyclic enones to produce highly functionalized cyclohexenones with very good degrees of diastereoselectivity and enantioselectivity.

Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity
Hua Yang, Somdev Banerjee and Rich G. Carter
DOI: 10.1039/C2OB25400J

The inside cover highlights the review of Brian Rasmussen and Jørn Bolstad Christensen that looks at the growing field of organocatalysis with dendrimers. This review outlines advances made in this area of organocatalysis and covers both interior- and surface-based examples, the catalysis of reactions ranging from functional group interconversion and C–C bond forming reactions to enzyme mimicking processes.

Organocatalytic dendrimers
Brian Rasmussen and Jørn Bolstad Christensen
DOI: 10.1039/C2OB25317H

Also featuring in this issue are several examples of our Organocatalysis web themed issue. Including the front cover article these are:

Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide
DOI: 10.1039/C2OB25431J, Communication

Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
DOI: 10.1039/C2OB25472G, Paper

Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated
DOI: 10.1039/C2OB25435B, Paper

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10 of the best: catalysis in Organic & Biomolecular Chemistry

04 Jun 2012

In this latest blog celebrating OBC’s 10th anniversary we bring to you a selection of 10 of the most highly cited articles that cover the area of catalysis. Every single one will be free to access for you to enjoy.

“Frustrated Lewis pairs”: a concept for new reactivity and catalysis
Douglas W. Stephan
DOI: 10.1039/B802575B

Asymmetric organocatalysis
Jayasree Seayad and Benjamin List
DOI: 10.1039/B415217B

The golden gate to catalysis
Anja Hoffmann-Röder and Norbert Krause
DOI: 10.1039/B416516K

Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
Yoshiji Takemoto
DOI: 10.1039/B511216H

Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
Alexander J. A. Cobb, David M. Shaw, Deborah A. Longbottom, Johan B. Gold and Steven V. Ley
DOI: 10.1039/B414742A

Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions
Guy C. Lloyd-Jones
DOI: 10.1039/B209175P

Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis
Amir H. Hoveyda, Dennis G. Gillingham, Joshua J. Van Veldhuizen, Osamu Kataoka, Steven B. Garber, Jason S. Kingsbury and Joseph P. A. Harrity
DOI: 10.1039/B311496C

σ-Chelation-directed C–H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover
Jin-Quan Yu, Ramesh Giri and Xiao Chen
DOI: 10.1039/B611094K

Primary amino acids: privileged catalysts in enantioselective organocatalysis
Li-Wen Xu and Yixin Lu
DOI: 10.1039/B803116A

[2.2]Paracyclophane derivatives in asymmetric catalysis
Susan E. Gibson and Jamie D. Knight
DOI: 10.1039/B300717K

Do you remember these articles? Have they influenced your work? Share your comments below, we would love to read them.

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OBC issue 24 now available, featuring oligonucleotides and self-sorting on the covers

31 May 2012

This week’s OBC front cover highlights the review of Sabine Müller and colleagues who discuss the methods for the preparation of oligonucleotides. In particular Müller et al. review the work done in the field of synthesis of trinucleotide synthons representing codons for the 20 canonical amino acids and their use for fully controlled partial or total randomization individually at any number of arbitrarily chosen codon positions of a given gene.

Mixed oligonucleotides for random mutagenesis: best way of making them
Tamil Selvi Arunachalam, Claudia Wichert, Bettina Appel and Sabine Müller
DOI: 10.1039/C2OB25328C

On the inside fron cover Manik Lal Saha and Michael Schmittel present a review on the emerging principles of how to guide several components toward the formation of self-sorted multi-component architectures, and in whcih they focus on developing a systematic classification for the reported self-sorting systems and an evaluation of their degree of self-sorting

Degree of molecular self-sorting in multicomponent systems
Manik Lal Saha and Michael Schmittel
DOI: 10.1039/C2OB25098E

Both of these reviews will be free to access for the next 6 weeks so get reading!

Also in this issue is the HOT communication by Marco Bella et al. regarding a modern take on the Rabe animation utilising organocatalyisis.

The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds
Daniele M. Scarpino Schietroma, Mattia R. Monaco, Valerio Bucalossi, Philipp E. Walter, Patrizia Gentili and Marco Bella
DOI: 10.1039/C2OB25595B

View the whole issue here….

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