Author Archive

A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes

A collaboration between research groups in UK, Spain and Italy led by Steven Nolan reveals the mechanism of the Au (I) catalysed formation of substituted indenes.

Read the conclusions of this mechanistic and computational study in this free to access until mid-January paper that is the inside cover of OBC Issue 1 2011.

Enjoy it!

A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes
Pierrick Nun, Sylvain Gaillard, Albert Poater, Luigi Cavallo and Steven P. Nolan
Org. Biomol. Chem., 2011, 9, 101-104
DOI: 10.1039/C0OB00758G

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Accessing quaternary carbon centres

Thomas Nugent and colleagues at Jacobs University describe the use of a three component catalyst, an amino acid, a base and a hydrogen bond donor, to form quaternary C-C bonds in this paper that is the front cover of the first issue of Organic & Biomolecular Chemistry in 2011.

Read this free to access until mid-January paper to find out more about the catalytic enantioselective formation of an important class of Michael products bearing quaternary carbons.

Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts
Thomas C. Nugent, Mohammad Shoaib and Amna Shoaib
 Org. Biomol. Chem., 2011, 9, 52-56
DOI: 10.1039/C0OB00822B, Communication

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Welcome to the Fluorine Chemistry Themed Issue

View the Fluorine Chemistry web themed issue

The RSC Fluorine Interest group celebrates its tenth anniversary.
In the past 10 years, we have witnessed a steady expansion of academic departments, institutes, scientific societies and special journal issues, all geared towards the promotion of fluorine chemistry. We have been thrilled to be part of this amazing period in the evolution and vitalisation of the field.

The group was launched in 2000 with Professor John M. Winfield (University of Glasgow) as its first Chair with the goals of providing a platform to encourage the highest-calibre research in fluorine chemistry in the UK and abroad, raising international visibility of the field and fostering the development of a broader community of fluorine chemists. Following John’s steps, Professor David O’ Hagan contributed to this mission as the second Chair of the group. 

The RSC Fluorine Prize was initiated in 2005 and rapidly gained international recognition. We are gratified by the positive feedback that we have received this far on the Fluorine group and the Prize, in particular, which has attracted outstanding winners since its creation (Professor Norio Shibata 2005, Professor Thomas Braun 2007 and Professor Jinbo Hu 2009).
Our well-established annual Postgraduate Meeting has also increased our visibility over the years, gathering all ages of fluorine chemists from the UK and overseas.

On this occasion, I would like to express my sincere gratitude to all our sponsors and members, who have supported the Fluorine Group in many ways and thereby contributing to the expansion of the field in the past ten years.

This web-themed anniversary issue, published across several RSC journals, illustrates a breadth of original research in the field from fundamental to applied science covering aspects of inorganic, organic, physical and medicinal fluorine-based chemistry. Some remarkable recent achievements of fluorine chemistry are showcased giving a unique overview of the many possibilities that this element offers.

I wish to express my sincere and deep appreciation to all of you who have supported our Group and contributed a paper to celebrate this 10th anniversary.  Reading your contribution was not only a pleasure but will also undoubtedly stimulate future developments in this exciting field of research.

Thanks for your support and for sharing our enthusiasm for fluorine chemistry.

Oxford

December 9, 2010

Professor Véronique Gouverneur

Chair RSC Fluorine Group

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Natural product articles in the next OBC issue

The first issue of Organic & Biomolecular Chemistry 2011 (coming soon) is another very impressive and high quality issue that contains top articles by very well respected scientists in the field of organic chemistry.

Here you have an advance: A list of the articles in the issue that deal with natural products.

Take a look at them and keep an eye on this successful first issue coming later this week.

Total syntheses of subereamollines A and B
James W. Shearman, Rebecca M. Myers, James D. Brenton and Steven V. Ley
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00636J, Communication

First total synthesis of antrocamphin A and its analogs as anti-inflammatory and anti-platelet aggregation agents
Chia-Lin Lee, Chi-Huan Huang, Hui-Chun Wang, Da-Wei Chuang, Ming-Jung Wu, Sheng-Yang Wang, Tsong-Long Hwang, Chin-Chung Wu, Yeh-Long Chen, Fang-Rong Chang and Yang-Chang Wu
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00616E, Communication

First total synthesis of (−)- and (+)-6-O-desmethylantofine
Meng Wu, Ling Li, Bo Su, Zhihui Liu and Qingmin Wang
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00287A, Paper

Computational and experimental investigations of mono-septanoside binding by Concanavalin A: correlation of ligand stereochemistry to enthalpies of binding
Michael R. Duff Jr., W. Sean Fyvie, Shankar D. Markad, Alexandra E. Frankel, Challa V. Kumar, José A. Gascón and Mark W. Peczuh
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00425A, Paper

Synthesis and NMR spectroscopic analysis of acylated pentasaccharide fragments of mycobacterial arabinogalactan
Chunjuan Liu, Michele R. Richards and Todd L. Lowary
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00423E, Paper

Synthesis and assignment of stereochemistry of the antibacterial cyclic peptide xenematide
Kuo-yuan Hung, Paul W. R. Harris, Amanda M. Heapy and Margaret A. Brimble
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00315H, Paper

Total synthesis of (−)-20-epiuleine via stereocontrolled one-pot asymmetric azaelectrocyclization followed by novel 1,4-addition reaction
Taku Sakaguchi, Shohei Kobayashi and Shigeo Katsumura
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00627K, Paper

Synthesis of dysideaproline E using organocatalysis
Ernest Owusu-Ansah, Amanda C. Durow, John R. Harding, Angela C. Jordan, Susan J. O’Connell and Christine L. Willis
 Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00617C, Paper

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Introducing 18F in amino acids

Véronique Gouverneur and colleagues at University of Oxford, UK,  have designed an excellent avenue to generate 18F-labelled molecules via traceless Staudinger ligation.

This OBC HOT article is free to access until the end of the year. The referees rated it as very significant and the authors say that this novel prosthetic group 18F-radiochemistry may find numerous applications in the context of peptide 18F-labelling as the new functionality installed upon ligation is the native amide bond.

This article is part of the fluorine chemistry web themed issue that will be published on line in December. Watch out for it and if you want us to let you know when it is published contact us.

The traceless Staudinger ligation for indirect 18F-radiolabelling
Laurence Carroll, Sophie Boldon, Romain Bejot, Jane E. Moore, Jérôme Declerck and Véronique Gouverneur
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00564A , Paper

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Mimic for DNA synthesis

Piet Herdewijn from the Catholic University of Leuven, Belgium, and colleagues have designed a series of leaving groups that are compatible with HIV-1 reverse transcriptase (an enzyme that synthesises DNA from RNA).

The manuscript has been highlighted in Highlights on Chemical Biology and it is also a OBC Hot article which will be free to access until the end of the year.

Tha referees said that it was a VIP paper that made a very important contribution to the field.

Read more here

3-Phosphono-L-alanine as pyrophosphate mimic for DNA synthesis using HIV-1 reverse transcriptase
Shiqiong Yang, Mathy Froeyen, Eveline Lescrinier, Philippe Marlière and Piet Herdewijn
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00554A , Paper

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Push-Pull cyclophanes: Thermodynamic studies on these NLO materials

Daniel Häussinger, Marcel Mayor and co-workers at University of Basel in Switzerland look at the physical organic aspects of push-pull biaryls and their dynamic conformational interchange for the preparation of bulk organic materials that will display non-linear optical activities.

Two main physical properties are crucial for a strong nonlinear optic response: a large hyperpolarizability of the chromophore and a noncentrosymmetric centre.

In this HOT paper, the authors describe the rotational barriers for atropisomer interconversion in a series of cyclophane derivatives functionalized with complementary electron donating/withdrawing substituents. The referees said that it was a very significant paper in the fied.

You can now read it for free until the end of the year.

Racemisation dynamics of torsion angle restricted biphenyl push-pull cyclophanes
Jürgen Rotzler, Heiko Gsellinger, Markus Neuburger, David Vonlanthen, Daniel Häussinger and Marcel Mayor
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00650E, Paper

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Making sun resistant clothes pegs hangs out in the press

We are very glad to say that this OBC paper by Michelle Coote and coworkers at the Australian National University in Camberra, has been highlighted in many different media outlets.

From the OBC editorial office we wanted to congratulate Michelle and her group.

The article will be free to access until the end of the year.

Revising the mechanism of polymer autooxidation
Ganna Gryn’ova, Jennifer L. Hodgson and Michelle L. Coote
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00596G , Paper

This article is part of a special web themed issue on radical chemistry that will be published shortly in memory of Professor Athel Beckwith and in recognition of his many distinguished contributions to chemistry. If you want to receive an e-mail when this special web themed issue is on-line do let us know.

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A threat for oral thrush: Cooperative regulation of mouth microbes

The very successful OBC Communication by Robert H. Cichewicz and coworkers, at the University of Oklahoma, on mutanobactin A and its influence on the yeast-mycelium transition of Candida albicans is now the inside cover of Issue 24.

These are just some examples of the web pages where this amazing article has been highlighted:

Congratulations to the authors on delivering such a great piece of research!

Read the original paper free to access until next year:

Mutanobactin A from the human oral pathogen Streptococcus mutans is a cross-kingdom regulator of the yeast-mycelium transition
P. Matthew Joyner, Jinman Liu, Zhijun Zhang, Justin Merritt, Fengxia Qi and Robert H. Cichewicz
Org. Biomol. Chem., 2010, 8, 5486-5489
DOI: 10.1039/C0OB00579G , Communication

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First total synthesis of two furanosesquiterpenes

Rajeev Menon and Martin Banwell at the Australian National University in Camberra have identified a novel and highly efficient Au (I) catalysed intramolecular Michael addition reaction that is a key step towards the first total synthesis of crassifolone and dihydrocrassifolone.

These two natural products can be extracted from the wood of the tree Myoporum Crassifolium that grows in Noumea, New Caledonia.  So now there is no need to go to this paradisiac beach to get these two natural products – you just need to get the white lab coat and safety googles on and go to the lab! 🙂

‘This unprecedent reaction may represent a useful new protocol for the construction of other terpenoids incorporating an annulated furan core’, say the authors of the paper.

Read it free to access until next year!

Total syntheses of the furanosesquiterpenes crassifolone and dihydrocrassifolone via an Au(I)-catalysed intramolecular Michael addition reaction
Rajeev S. Menon and Martin G. Banwell
Org. Biomol. Chem., 2010, 8, 5483-5485
DOI: 10.1039/C0OB00487A

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