Author Archive

On the cover: a mild route to [2.2]paracyclophanes

On the cover of Issue 14 is work from Dario Pasini and colleagues at the University of Pavia.  They have designed a new route to the synthetically challenging cyclophane, [2.2]cyclophanediene.   By using a Pummerer rearrangement of the [3.3]dithiacyclophane starting material, followed by sulfur extrusion the group were able to demonstrate the applicability of this mild and high yielding route.

For the full details download the article – it’s free to access for 6 weeks:

Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement
Matteo Montanari, Alberto Bugana, Arvind K. Sharma and Dario Pasini
Org. Biomol. Chem., 2011, 9, 5018-5020
DOI: 10.1039/C1OB05319A

View the issue here

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Work on bacterial lipoteichoic acids in the press!

The hot Perspective article from Richard Schmidt, Christian Pedersen, Yan Qiao and Ulrich Zähringer has been picked up by several media outlets interested in their work on bacterial lipoteichoic acids.

The team reported the synthesise of several LTAs – which are important important constituents of the cell wall of Gram-positive bacteria – and carried out studies on their biological activity.  More work is needed to understand the recognition of LTAs by the innate immune system, but this work suggests that it is indeed the lectin pathway that LTAs interact with and paves the way for an improved understanding of infection by Gram-positive bacteria.

Here are some of the places the research has been highlighted:

Download the original Perspective article here for all the details:

Chemical synthesis of bacterial lipoteichoic acids: An insight on its biological significance
Richard R. Schmidt, Christian M. Pedersen, Yan Qiao and Ulrich Zähringer
Org. Biomol. Chem., 2011, 9, 2040-2052
DOI: 10.1039/C0OB00794C

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Top cited OBC articles free to access!

The OBC Editorial Office has collected together the top 5 most cited papers in the last 5 years, and they are now free to access.

Our congratulations and thanks to the authors!

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
Org. Biomol. Chem., 2005, 3, 84-96
DOI: 10.1039/B414742A, Paper

Synthesis and photophysical evaluation of charge neutral thiourea or urea based fluorescent PET sensors for bis-carboxylates and pyrophosphate
Thorfinnur Gunnlaugsson, Anthony P. Davis, John E. O’Brien and Mark Glynn
Org. Biomol. Chem., 2005, 3, 48-56
DOI: 10.1039/B409018G

Urea vs. thiourea in anion recognition
David Esteban Gómez, Luigi Fabbrizzi, Maurizio Licchelli and Enrico Monzani
Org. Biomol. Chem., 2005, 3, 1495-1500
DOI: 10.1039/B500123D, Paper

Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones
Wei Chen, Wei Du, Lei Yue, Rui Li, Yong Wu, Li-Sheng Ding and Ying-Chun Chen
Org. Biomol. Chem., 2007, 5, 816-821
DOI: 10.1039/B616504D, Paper

Enantioselective Friedel–Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst – synthesis of optically active tetrahydro-β-carbolines
Wei Zhuang, Rita G. Hazell and Karl Anker Jørgensen
Org. Biomol. Chem., 2005, 3, 2566-2571
DOI: 10.1039/B505220C, Paper

Want to be in the next top 5? Then why not submit to us today!

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: a neat new route to the integrastatin core

Integrastatins display micromolar inhibition of the HIV-1 integrase enzyme, halting replication of the virus.  Medicinal chemists are therefore very interested in being able to synthesise these natural products, and their analogues, to investigate potential HIV therapies.

The total synthesis of either integrastatin A or B is yet to be reported, but several groups have reported the synthesis of the tetracycle core, Brian Stoltz and colleagues Caltech being the latest.   Their synthesis differs from previous reports by utilising a palladium-catalyzed oxidative cyclization.  Their four-step route produces the tetracycle core in 30% overall yield.

This HOT piece of synthesis is free to access for 4 weeks:

A rapid and convergent synthesis of the integrastatin core
Pamela M. Tadross, Pradeep Bugga and Brian M. Stoltz
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05725A

You may also like to look at the other reports of the integrastatin core synthesis published in RSC journals:

Unexpected Z-stereoselectivity in the Ramberg–Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus
Jonathan S. Foot, Gerard M. P. Giblin, A. C. Whitwood and R. J. K. Taylor
Org. Biomol. Chem., 2005, 3, 756-763

An expeditious one-step entry to the tetracyclic core of integrastatins
C. V. Ramana, Challa Nageswara Reddy and Rajesh G. Gonnade
Chem. Commun., 2008, 3151-3153

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

An easy route to tetrahydrofluorene scaffolds on the cover of Issue 13

View the issue here

The article highlighted on the cover of our latest issue is work from Gautam Panda and Ritesh Singh at the Central Drug Research Institute, India.

They have reported an efficient, regioselective route to hetero [6,5,6]ABC tetrahydrofluorene cores.  This type of tricyclic hydrofluorene core is found in a class of natural products called Taiwaniaquinoids, which have shown some promising bioactivities.

To access the hetero tetrahydrofluorene skeleton the authors used divinyl alcohols, activated with Sc(OTf)3 in a Nazarov-type cyclisation achieving the desired scaffold under very mild conditions.

Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids
Ritesh Singh and Gautam Panda
Org. Biomol. Chem., 2011, 9, 4782-4790
DOI: 10.1039/C0OB00892C

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Dioxazaborocanes: old adducts, new tricks

This Emerging Area article from Hélène Bonin and Emmanuel Gras (CNRS) discusses the recent developments in dioxazaborocane chemistry that the authors believe may make it a viable fluoride-free alternative to organotrifluoroborate salts.

The review covers the synthesis and properties as well as the applications of dioxazaboracanes in organic chemistry.  The recent uses of dioxazaboracanes as direct reactants, rather than as boronic ester or acid protecting groups, are highlighted and the authors hope that a better understanding of their structures in solution will increase the use of these compounds in direct synthesis.

Dioxazaborocanes: old adducts, new tricks
Hélène Bonin, Thomas Delacroix and Emmanuel Gras
Org. Biomol. Chem., 2011,
DOI: 10.1039/C1OB05330B

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Most cited OBC Perspective articles free to access!

The OBC Editorial team has collected the most cited Perspectives published in our journal in the last 5 years and you can now download them for free!

Perspective articles are either a concise and critical appraisal, or a personal viewpoint of activity in a specialist area of organic chemistry of current interest, and are not intended to be comprehensive reviews of the literature. They are normally published by invitation of the Editorial team but suggestions from authors are welcome and enquiries should be directed to the Editor.

Find the top 5 most cited Perspectives in the last 5 years below. Our congratulations and thanks to the authors!

Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
Yoshiji Takemoto
Org. Biomol. Chem., 2005, 3, 4299-4306
DOI: 10.1039/B511216H

DNA-programmed assembly of nanostructures
Kurt V. Gothelf and Thomas H. LaBean
Org. Biomol. Chem., 2005, 3, 4023-4037
DOI: 10.1039/B510551J

Bifunctional transition metal-based molecular catalysts for asymmetric syntheses
Takao Ikariya, Kunihiko Murata and Ryoji Noyori
Org. Biomol. Chem., 2006, 4, 393-406
DOI: 10.1039/B513564H

Analysis of the reactions used for the preparation of drug candidate molecules
John S. Carey, David Laffan, Colin Thomson and Mike T. Williams
Org. Biomol. Chem., 2006, 4, 2337-2347
DOI: 10.1039/B602413K

Density functional theory with dispersion corrections for supramolecular structures, aggregates, and complexes of (bio)organic molecules
Stefan Grimme, Jens Antony, Tobias Schwabe and Christian Mück-Lichtenfeld
Org. Biomol. Chem., 2007, 5, 741-758
DOI: 10.1039/B615319B

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: glycosyldisulfide lectin ligands

S-glycosides are resistant to hydrolytic cleavage, which gives them a distinct pharmacological advantage over O-glycosides as ligands for lectins, but inherently present different biological activity.  This HOT article evaluates the ability of dithiodigalactoside (DTDG) – which was identified through a dynamic combinatorial library approach in a previous study – to protect human cells from toxin binding.

Jésus Jiménez-Barbero, CSIC, and an international team of researchers show that DTDG is capable of selecting between the mistletoe toxin and human lectins and conclude that glycosyldisulfides have potential as chemical platform for inhibitor design.

Interested? The article is free to download for the next 4 weeks:

Symmetric dithiodigalactoside: strategic combination of binding studies and detection of selectivity between a plant toxin and human lectins
Sonsoles Martín-Santamaría, Sabine André, Eliza Buzamet, Rémi Caraballo, Gloria Fernández-Cureses, Maria Morando, João P. Ribeiro, Karla Ramírez-Gualito, Beatriz de Pascual-Teresa, F. Javier Cañada, Margarita Menéndez, Olof Ramström, Jesús Jiménez-Barbero, Dolores Solís and Hans-Joachim Gabius
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB01235A

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

OBC Issue 12 now available online!

View the issue online here

On our cover this issue is work from Silvia Schenone (University of Genoa, Italy) describing the separation of enantiomers of newly-synthesised A1 adenosine antagonists.  The group had previously synthesised a family of pyrazolo[3,4-b]pyridine derivatives, and here show that the enantiomers of the most active compound have different affinity for the receptor.

Substituted pyrazolo[3,4-b]pyridines as human A1 adenosine antagonists: Developments in understanding the receptor stereoselectivity
Tiziano Tuccinardi, Alessandra Tania Zizzari, Chiara Brullo, Simona Daniele, Francesca Musumeci, Silvia Schenone, Maria Letizia Trincavelli, Claudia Martini, Adriano Martinelli, Gianluca Giorgi and Maurizio Botta
Org. Biomol. Chem., 2011, 9, 4448-4455
DOI: 10.1039/C0OB01064B

As with all our cover articles, this paper is free to access for 6 weeks – why not download it today!

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: ultra-sensitive fluorescence quenching to detect molecular recognition events

Achieving sensitive signal detection in fluorescence-based assays often involves chemically pre-amplifying the signal to detectable levels.   There are currently several methods of achieving amplification, but here Andrei Kutateladze and colleagues at the University of Denver come up with a concept different from previous methods based on photoamplified fluorescence quenching.

General concept for the amplified unmasking of benzophenone resulting in fluorescence quenching

They are able to detect molecular recognition events in the biotin-avidin system through the autocatalytic photo-unmasking of benzophenone – which acts as both the amplification chain carrier and the quencher for the reporter fluorophore – achieving attomolar detection limits with a relatively cheap CCD camera.  They even demonstrate the possibility of imaging the binding assay with an ordinary mobile phone camera, showing that sensitive analysis can be carried out when expensive state-of-the-art equipment is not available.

To read more, download the article – it’s free to access for the next four weeks:

Photochemically amplified detection of molecular recognition events: an ultra-sensitive fluorescence turn-off binding assay
Tiffany P. Gustafson, Greg A. Metzel and Andrei G. Kutateladze
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05289F

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)