Nominations for the 2012 RSC Prizes and Awards close on the 15 January 2012
Our Prizes and Awards represent the dedication and outstanding achievements and are a platform to showcase inspiring science to gain the recognition deserved. Don’t forget to nominate colleagues who have made a significant contribution to advancing the chemical sciences.
View our full list of Prizes and Awards and use the online system to nominate a colleague.
Welcome to Issue 1 of OBC, 2012!
On the front cover we have an article from Brian Stolz and team on the synthesis of enantioenriched γ-quaternary cycloheptenones, with potential for the preparation of non-natural analogs of cycloheptanoid natural products.
Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems
Nathan B. Bennett, Allen Y. Hong, Andrew M. Harned and Brian M. Stoltz
DOI: 10.1039/C1OB06189E
On the inside front cover is an article from Robert Stockman and coworkers. They report the synthesis of an advanced intermediate, an azaspirocyclic aldehyde, in the route to halichlorine developed by Clive and coworkers, shortening the synthetic route by 15 steps.
Combining two-directional synthesis and tandem reactions: a short formal synthesis of halichlorine
Camille Gignoux, Annabella F. Newton, Alexandre Barthelme, William Lewis, Marie-Lyne Alcaraz and Robert A. Stockman
DOI: 10.1039/C1OB06380D
Incredibly 2012 will be our 10th year of publication and we would like to thank all our authors, referees, readers and Board members for their support over the last decade. Read the Editorial introduction to the next volume from Chair Jeffrey Bode and Editor Richard Kelly for the changes we’ve seen and what we have to look forward to in the coming year.
The publication this week of OBC’s first issue of 2012 sees the journal doubling its frequency to 48 issues per year.
Since 2003 OBC has built on its core values of high impact research, good author service and rigorous, fair and timely peer review to grow into one of the leading journals in the field. It’s no surprise therefore that in the last four years the number of authors choosing to publish their articles with OBC each year has more than doubled. To accommodate this increased content we will now be publishing issues weekly.
To receive weekly updates on the latest research published in OBC, sign-up for our contents alerts.
A concise synthesis of the natural product rasfonin could reignite interest in this molecule as a tool to develop cancer drugs, say scientists from the Netherlands.
Adriaan Minnaard and Ben Feringa’s group from the University of Groningen developed the synthesis, which has a higher overall yield and takes fewer steps than previous syntheses, they say.
Rasfonin could be important in cancer research because it inhibits a cell signalling pathway called the RAS pathway. ‘If a cell becomes cancerous, often you see that RAS, the most important protein in the pathway, is mutated,’ explains Minnaard. The mutated RAS keeps on signalling, so the cancer cells keep dividing. Rasfonin blocks the pathway by binding either to RAS or one of the other proteins in the pathway, but it’s not known which one. ‘Scientists would love to have rasfonin to investigate this further, but it takes too much time and effort to make,’ says Minnaard.
In a bid to make synthesis easier, the team has made rasfonin in 30 steps (21 in the longest linear sequence) and in 11 per cent overall yield. ‘It’s quite a lot of steps,’ admits Minnaard, ‘but given the overall yield and the good activity (which means that not so much compound is needed), the synthesis is suitable to prepare any quantity needed for research purposes.’ One main step was introducing the methyl groups in the upper chain of rasfonin using catalytic asymmetric conjugate addition and the other was forming the lower chain, which involved using Feringa butenolide, a building block developed by Feringa. ‘It makes our synthesis much more straightforward than the current two syntheses,’ says Minnaard.
The synthesis of rasfonin was developed using asymmetric conjugate addition and Feringa's butenolide
The first synthesis in 2003 elucidated the stereochemistry and structure of rasfonin, but was not aimed at creating a synthesis for producing large quantities. Masami Ishibashi from Chiba University, Japan, who carried out this synthesis, says that Minnaard and Feringa have achieved a highly stereoselective and efficient synthesis. ‘It may be strongly expected that this new route will accelerate the chemical biology of rasfonin to identify its target protein,’ says Ishibashi.
‘It is a nice piece of work, which highlights some of the asymmetric catalysis methods developed in Professor Feringa’s laboratory,’ adds Robert Boeckman from the University of Rochester, US, who carried out the second synthesis of rasfonin in 2006. Boeckman’s synthesis used chiral auxiliaries. ‘Boeckman changes the substrate in such a way that the stereochemical outcome will be the desired one, but he has to do a lot more steps with the substrates,’says Minnaard. ‘We have our information in the catalyst, which is more efficient.’
Interested? Read Elinor Richards’ full Chemistry World article here or download the OBC paper:
A concise asymmetric synthesis of (−)-rasfonin
Yange Huang, Adriaan J. Minnaard and Ben L. Feringa
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06700A
We are delighted to announce the appointment of two new Associate Editors, Professor Jin-Quan Yu and Professor Andrei Yudin, to handle manuscripts for OBC.
Professor Jin-Quan Yu has worked at the Scripps Research Institute since July 2007, where his research centres around the discovery of novel reactions based on C-H activation. Prior to this he held an Assistant Professorship at Brandeis University and has also worked at the University of Cambridge where he received his PhD under the supervision of Professor Jonathan B. Spencer.
Jin-Quan Yu has received numerous awards throughout his career, most recently the 2012 Mukaiyama Award, the 2012 Arthur C. Cope Scholar Award, and the 2011 Novartis Early Career Award. He has authored over 85 publications to date, many of which have been highlighted in the scientific press.
Professor Andrei Yudin obtained his B.Sc. degree at Moscow State University and his Ph.D. degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah. He subsequently took up a postdoctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. He received early tenure, becoming an Associate Professor in 2002, and received an early promotion to the rank of a Full Professor in 2007.
Amongst Professor Yudin’s awards are the CSC Award in Combinatorial Chemistry, the 2004 Amgen New Faculty Award, the 2010 CSC Merck-Frosst Therapeutic Center Award, the 2010 Rutherford Medal of the Royal Society of Canada, and the 2011 University of Toronto Inventor of the Year Award.
The appointment of the two Associate Editors to the OBC Board means that authors now have a choice of submission routes when sending their articles to the journal. Using our online submission system, authors can choose for their articles to be handled by either Professor Yu, Professor Yudin (from October), or a Publishing Editor at the Cambridge Editorial office. More details on the submission procedures for OBC can be found in the journal’s guidelines.
This week, the RSC launched a new product, RSC e-membership, allowing anyone to access an electronic version of Chemistry World through a MyRSC account and to enjoy the benefits of electronic networking via this professional online community for £20/year.
Subscribers to this do not benefit from the professional recognition or any of the other many services and discounts available to RSC Members, but it allows chemists from around the world, many already members of another chemical society in their own country, to benefit from the highly-esteemed content in Chemistry World and the networking opportunities offered from MyRSC, which now stands at over 11,000 members. The RSC e-membership also allows subscribers to join a virtual specialist interest group on MyRSC. If you are interested in joining, please visit www.rsc.org/emembership.
We are delighted to announce a forthcoming ChemComm–Organic & Biomolecular Chemistry (OBC) web themed issue:
Organocatalysis
Guest editors: Keiji Maruoka (Kyoto University), Hisashi Yamamoto (University of Chicago), Liu-Zhu Gong (University of Science and Technology of China) and Benjamin List (Max-Planck-Institut für Kohlenforschung)
Submission deadline: 29th February 2012
We are now inviting submissions for this web theme, which will be a celebration of current achievements and future perspectives in this exciting field of research.
ChemComm and OBC are both welcoming urgent communications; OBC also welcomes full papers. Please feel free to submit to either or both journals.
All manuscripts will undergo strict peer review and should be very important and conceptually significant in accord with the ChemComm and OBC mandates.
Publication of the peer-reviewed articles will occur without delay to ensure the timely dissemination of the work. The articles will then be assembled on the RSC Publishing Platform as a web-based thematic issue, to permit readers to consult and download individual contributions from the entire series.
Communications for this web theme can be submitted anytime from now until 29th February using ChemComm’s and OBC’s web submission system. Please add the phrase ‘organocatalysis web theme‘ in the comments to the editor field.
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
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!
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.
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
