Archive for the ‘Organic’ Category

Organocatalysis – announcing a joint ChemComm–OBC web theme

We are delighted to announce a forthcoming ChemCommOrganic & 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.

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Tetrafluorocyclohexane: a novel polar motif

The cyclohexane motif is among the most common in organic chemistry but selectively fluorinated versions are rare. The high polarity of C–F bonds can influence the conformation and reactivity of molecules, making fluorinated molecules high on the target list of many chemists, including David O’Hagan at the University of St Andrews, UK.

His team have managed to make 1,2,3,4-tetrafluorocyclohexane, the first example of a cyclohexane with more than two vicinal fluorine atoms. The all syn stereochemistry forces two of the C–F bonds into 1,3-diaxial orientations. This diaxial interaction makes the molecule polar, which O’Hagan suggests could make it a novel polar structural motif for organic materials.

Graphical abstract: Synthesis and structure of all-syn-1,2,3,4-tetrafluorocyclohexane

Find out more: download O’Hagan’s ChemComm communication for free until 28th July.

Also of interest: Fluorine chemistry web theme

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Totally synthetic over bryostatin

Bryostatins are macrocyclic natural products with various biological activities, including potent anti-cancer activity due to protein kinase C inhibition. Eric Thomas and his team from the University of Manchester have shown that it is possible to prepare 20-deoxybryostatin, using a modified Julia olefination to form the tricky 16,17-double-bond, followed by macrolactonisation, selective deprotection and oxidation.Fancy finding out more about the reaction conditions?

Download the ChemComm communication, which will be free to access until the 1st July 2011. 

20-deoxybryostatin

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Ibuprofen: anticancer drug

Scientists in the UK have moved a step closer to understanding how ibuprofen could help treat cancer. The findings could lead to the drug being used as a preventative treatment for prostate cancer, in the future.

Ibuprofen – a common painkiller – can help reduce the risk of prostate cancer, but the mechanism by which it inhibits tumour cells is still not fully understood. Now, Matthew Lloyd and his team from the University of Bath in the UK, in collaboration with Cancer Research UK, have uncovered a mechanism suggesting that the chiral inversion of ibuprofen inhibits the activity of the protein alpha-methylacyl-CoA racemase (AMACR), levels of which are increased in the presence of prostate, some colon and other cancers.

To find out more, read the full news story in Chemistry World and download Lloyd’s ChemComm communication.

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Final stop for the ChemComm Symposium

The international speakers assembled early on Thursday morning to make the final journey to Nankai University, Tianjin. After a flight and a two hour journey on the ChemComm minibus, we arrived at our hotel directly opposite the entrance gates to Nankai University. The first thing that struck us about the hotel was the enormous rooms. I actually got lost in mine between the two bathrooms, the study and the lounge area. Apparently they were all like this – what a hotel!

After a formal dinner with our host Professor Qilin Zhou (Director of the State Key Laboratory of Elemento-organic Chemistry and member of the Chinese Academy of Sciences), most retired to bed but Professor Rawal, Professor Maruoka and I were taken to a live Chinese comedy show. Lots of clapping with plastic clapping hands, much laughter and, of course, all sketches in Chinese. It was a great experience even if we did not understand anything apart from ‘hello’ and ‘thank you’.

The following day started with eager anticipation as an audience in excess of 100 watched Professor Feringa give his final scientific presentation on motors and switches. He was followed by local Professor of Energy, Yun Chen, who spoke about some of his latest research into new nanomaterials for batteries, a key challenge with the ever increasing energy demands around the world. Before lunch, Veronique Gouverneur gave her presentation looking at the latest developments in organofluorine chemistry.

After lunch, the five poster judges took to their duties for one last time with each asked to examine ten posters and select just one. With the final five selected it was left to Professors Feringa and Maruoka to rank the winners. All five received money from the State Key Lab thanks to the generosity of Professor Zhou, plus journal subscriptions and books from the RSC, amongst other things, as additional gifts.

The scope of the meeting then switched to green chemistry as Professor Buxing Han spoke about his latest research using ionic liquids, supercritical fluids and a mixture of the two as solvents for organic reactions. Professor Han was followed by Professor Rawal who gave his third different talk in five days covering his group’s total synthesis of a member of the Welwitindolinone group of natural products. This was a particularly insightful talk as Professor Rawal not only discussed things that worked but also routes that had failed. There was certainly a good lesson here for total synthesis students, namely things may not always work out but perseverance is the key to success.

In the last session of the day, Professor Maruoka spoke about some of his latest results in the field of organocatalysis. He was followed by Zhen Yang who gave a second total synthesis masterclass. The retrosynthetic analysis slides certainly gave me a trip down memory lane and the overall synthesis in 26 steps (micrandilactone) showcased the real power of organic chemistry and the creative thought processes needed to succeed.

After the poster presentations had been made, the speakers and other key faculty members walked to a very famous restaurant called Goubuli for steamed dumplings. They are a local speciality, filled with vegetables, fish and, traditionally, pork. Normally six is enough, but I was proud to exceed the average! The other highlight of the dinner was the stinky tofu, a delicacy providing you can get past the tremendously bad smell, much stronger than the bluest blue cheese. This was a real challenge – the stink was just so bad!

After dinner, the speakers and faculty members retired to a German bar for one last drink to celebrate the day and the past week. Over the course of the seven days we had travelled many thousand of miles, seen 21 scientific talks covering many different aspects of the chemical sciences, with a total audience close to 700 and nearly 200 posters judged. All in all, it was a great week and the only thing left to do is to thank all the speakers and, of course, the local hosts, without whom none of this would have been possible.

Robert Eagling

View the Nankai Symposium schedule

Related posts:

ChemComm Symposium heads west…..

The 5th ChemComm International Symposium gets underway….

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A refreshing limonoid synthesis

The challenging synthesis of B-seco limonoids has been achieved using an Ireland-Claisen rearrangement, report scientists in Germany.

Herbert Waldmann worked with a collaboration of scientists from various German science institutes on this project and believes that the synthetic strategy described here might facilitate the total synthesis of other natural products containing similar limonoid scaffolds and their analogues.

For more details on the reaction conditions used, download the ChemComm communication today, which will be free to access until the 24th June 2011.

You may also be interested to know that Herbert Waldmann recently helped guest edit a web themed issue on ‘Enzymes and Proteins’ – A nice collection of articles from high profile scientists in this area of chemical biology, including some of Herbert’s very own research papers.
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ChemComm Symposium heads west…..

A 5am start was always going to be tough, particularly after such a successful event in Kyoto. That said, with cases packed, we headed to Kansai Airport…. next stop Beijing!

After a three hour flight, the ChemComm International delegation arrived at Beijing International Airport where we had a four hour layover. After lunch, we were joined by the RSC Publisher for China, Dr Daping Zhang, and Professor Keiji Maruoka, the final international speaker for the next two events. The flight to Lanzhou was smooth and, to our delight, we were met by the former director of the Key State Laboratory and member of the Chinese Academy of Sciences, Professor Yong-Qiang Tu. Following a buffet dinner accompanied by excellent regional red wine, the speakers retired early with one eye on the second symposium

The following morning, we were greeted at the entrance to Lanzhou University with possibly the largest ChemComm advertising sign I have ever seen. ‘Big’ was certainly the theme of the day, with Professor Wei Wang informing speakers that an audience of around 400 was anticipated with 80 posters to review over lunch.

Professor Tu opened events and chaired the first session, inviting Professor Xinhe Bao to the stage. Professor Bao gave a beautiful overview on some of his very detailed studies into heterogenous catalysis within nanotubes and other nano-confined systems. Using nobel metals or metals such as iron or nickel, it was shown that the conversation of syngas was much more efficient inside the tube than outside. The subject of the session then switched to metal-free homogenous catalysis, as Professor Maruoka spoke about some of his latest results in the field of organocatalysis. As you would expect, high enatiomeric excesses and yields were the order of the day.

 Following coffee, Professor Veronique Gouverneur gave another whistle-stop tour of her group’s latest organofluorine chemistry and the formation of  C–F bonds using palladium and gold homogenous catalysis.

As in Kyoto, the speakers worked hard over lunch analysing the 80 posters on show. They covered everything from organic methodology, to total synthesis, organic materials and supramolecular chemistry. If they thought judging them was tough in Kyoto, it proved even more so in Lanzhou! Unfortunately, Professor Ben Feringa was unable to act as a judge, because, due to a last minute laptop crisis, his presentation was being transferred to a spare laptop, with his own laptop in pieces, being fixed by helpful student Mr Woo.

After lunch, the conference switched gears to total synthesis. Professor Dawei Ma spoke first about the total synthesis of galbulimima alkaloids and communesins. Professor Ma was followed by Professor Viresh Rawal, who gave a different talk to that described in the programme. Professor Rawal described his recent total synthesis of Pederin and Mycalamide B, both part of the Pederin family of natural products isolated from the beetle Paederus fuscipas. He also introduced initial work looking at bioactivity of Mycalamide in cells, carried out with Milan Mrksich

For the final session, the audience were treated to a masterclass from Ben Feringa on molecular motors and switches. This was only made possible by Mr Woo, who had rebuilt his computer, replacing a transistor, and bingo! His synthetic motors, inspired by nature, are unidirectional with the direction controlled by the enantiomer used. By adding legs, the motors can be bound to gold surfaces and then used to change the orientation of liquid crystal films. A great talk and even Professor Bao, the session Chair, could not bring himself to cut it short. Thank goodness for Mr Woo! The final talk of the day was presented by Professor Deqing Zhang on tetrathiafulvalene-based switchable molecular systems towards functional materials. 

The evening social events were as memorable as the science, with the speakers joined by 50 or so guests including the vice Dean of Lanzhou University. The Chinese banquet was enhanced with locally produced red wine and Chinese liquor (only to be drunk in multiples of three – Chinese style…kambai). After many toasts and speeches, the speakers were taken to a local pub for some traditional Chinese music. The night was not done, however, as we then moved to a Tibetan bar. The speakers were told to expect local singing and dancing. Little did they know that they would be involved! After being sung to, each speaker was presented with a white Hada. What a great way to end such a action-packed day.

Next stop Tianjin for the final event of three…..

Robert Eagling

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The 5th ChemComm International Symposium gets underway….

The 5th International ChemComm Symposium got off to an excellent start in Kyoto, Japan, on Monday (16th May) under the Chairmanship of ChemComm Editorial Board member and distinguished Professor Keiji Maruoka (Kyoto University).

World leading authorities from the USA, UK, the Netherlands, China and Japan arrived on Sunday in time to be treated to a ten course western-style dinner. The dinner was a perfect start to proceedings but even the ten courses could not over-shadow the science that was to follow.

With an audience in excess of 100, I opened the symposium and thanked the local organisers, speakers and poster presenters. Special thanks were also given to Professor Maruoka for all his support in organising the event. As the first session Chair, Professor Maruoka then got things underway.

Professor Tsutomu Katsuki (Kyushu University) was up first, speaking initially about oxidation chemistry using ruthenium but then moving, like nature, to iron, for example. He was followed by Professor Kuiling Ding (Shanghai Institute of Organic Chemistry) who gave a talk of two halves, covering his group’s ongoing efforts to overcome the challenging issues in both homogenous and heterogeneous asymmetric catalysis.

A quick stop for refreshments was followed by Professor Véronique Gouverneur (University of Oxford) who spoke about her ongoing efforts to develop transition metal-catalysed reactions to generate C–F bonds. Not easy, but made even more challenging by the fact that the methods need to be incredibly quick so they can be used to incorporate hot [18F], which has a very short half-life. Such [18F] labelled compounds are used in positron emission tomography.

Ben Feringa discussed a posterOver lunch, the seven speakers interacted with the 35 poster presenters, putting them through their paces, with the five lucky winners scheduled to be announced at the end of the day.

The pace of the event did not slow after lunch. Professor Viresh Rawal (University of Chicago) wowed a packed auditorium with some of his latest results using H-bonded systems for asymmetric catalysis. Before the break, Professor Zhengfeng Xi (Peking University) spoke about the synthesis, unique reactivity, cooperative effect and applications of organo-di-lithio reagents.

The symposium was closed first by Professor Atsuhiro Osuka (Kyoto University), who spoke about some of his beautiful results in the area of Möbius porphrin chemistry, and then by Professor Ben Feringa (University of Groningen). Professor Feringa gave a wonderful overview of some of the ongoing research in his lab exploring chiral space in asymmetric catalysis. Some highlights included the latest examples of C–H and C–C bond formation using monodentate phosphoramidite ligands and also new results in the field of asymmetric catalysis using DNA with his colleague Professor Gerard Roelfes. The later certainly generated a number of interesting questions about the length and sequence requirements of the DNA involved in the reactions.

symposium speakers, poster prize winners and chairmanAfter the formal poster prize presentations, the speakers and organising committee were treated to a traditional Japanese meal. Before dinner, the historic nature of the Japanese tea ceremony was explained in detail and served to the group by a Maiko (a young training Geiko). Through dinner, the speakers were also treated to some traditional Japanese singing and dancing performed by the Maiko. The music and dance showcased the four seasons of Kyoto.

The dinner finished with the speakers retiring to bed in preparation for their early flight first to Beijing and then Lanzhou, the next venue for the second of three ChemComm symposia.

Robert Eagling

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Antonio Echavarren joins the ChemComm Editorial Board

Antonio EchavarrenOn behalf of the ChemComm Editorial Board, I am delighted to welcome Professor Antonio Echavarren as the new ChemComm Associate Editor for organic chemistry and catalysis.

Professor Echavarren is Group Leader at the Institute of Chemical Research of Catalonia (ICIQ) in Tarragona, Spain. His research focuses on developing new catalytic methods based on the organometallic chemistry of transition metals as well as synthesing natural products and polyarenes.

Professor Echavarren’s editorial office is now open for submissions, welcoming urgent communications highlighting the latest advances in organic chemistry and catalysis.

Find out more about Professor Echavarren’s research on gold catalysis by reading these exciting articles:

A multipurpose gold(I) precatalyst
Mihai Raducan, Carles Rodríguez-Escrich, Xacobe C. Cambeiro, Eduardo C. Escudero-Adán, Miquel A. Pericàs and Antonio M. Echavarren, Chem. Commun., 2011, 47, 4893-4895

Mechanism of the gold-catalyzed cyclopropanation of alkenes with 1,6-enynes
Patricia Pérez-Galán, Elena Herrero-Gómez, Daniel T. Hog, Nolwenn J. A. Martin, Feliu Maseras and Antonio M. Echavarren, Chem. Sci., 2011, 2, 141-149

Are you an organic chemist based in North America? Submit your research to Michael Krische, ChemComm North American Associate Editor for organic chemistry.

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Call for communications: catalytic C–C bond formation via late transition metals

Michael KrischeChemComm Associate Editor Michael Krische is delighted to announce a forthcoming web themed issue:

New advances in catalytic C–C bond formation via late transition metals

Guest editor: Michael Krische (University of Texas at Austin)

Submission deadline: 30th September 2011

We are now welcoming submissions for this web theme, which will be a celebration of current achievements and future perspectives in this exciting field of research.

All manuscripts will undergo strict peer review and should be very important and conceptually significant in accord with the ChemComm mandate.

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 ChemComm website 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 30th September using our web submission system. Please add the phrase ‘catalytic C–C bond formation’ in the comments to the editor field.

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