Archive for April, 2012

OBC symposium concludes in Beijing

The final day of the OBC symposium saw us arrive at Peking University.

Professor Lei Liu presenting at Peking University

The day opened with PKU head of organic chemistry Professor Zhenfeng Xi welcoming us to the institute, and this was followed by Andrei Yudin’s final presentation and then Professor Guanxin Liang from Nankai University showing a variety of natural product syntheses from his lab. The morning was rounded off by Dirk Trauner.

The first afternoon session showcased the work of Professors from two institutes in Beijing. Professor Lei Liu from Tsinghua University presented on protein synthesis while Professor Sanzhong Luo from the Institute of Chemistry, Chinese Academy of Sciences showed his latest research on asymmetric binary-acid catalysis.

The second afternoon session saw OBC Chair Jeffrey Bode giving another demonstration of his research into amide-forming reactions, and then Professor Zhi-Xiang Yu from Peking University gave an interesting overview of the potential power of computational chemistry in natural products synthesis.

Our visit to Beijing was a great way to finish this first OBC symposium and we’re very grateful to local organiser Professor Jianbo Wang and all of the speakers.

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 Symposium moves to Lanzhou University

Following a successful first day in Shanghai, the OBC Symposium travelled to Lanzhou. On arrival we were greeted by a huge banner opposite the entrance. No one visiting the University would be in any doubt that OBC were in town!

The OBC symposium banner at the entrance to Lanzhou University

The day started with a welcome by Director of the State Key Laboratory of Applied Organic Chemistry at Lanzhou Professor Yongqiang Tu, which was followed by Dirk Trauner’s presentation on natural product synthesis. The morning was rounded-off by Professor Xiaoming Feng from Sichuan University, who guided us through his research on asymmetric catalysis using chiral N,N’-Dioxide ligands.

Professor Andrei Yudin at Lanzhou University

Following lunch Professor Hongbin Zhang from Yunnan University presented the syntheses of some bioactive alkaloids. Professor Tu then returned to the stage to continue the natural products synthesis theme by giving an overview of his work on syntheses which employ 1,2-migration reactions. Andre Yudin gave another overview of his work using amphoteric molecules and the final talk of the day was given by Professor Hanmin Huang from Lanzhou Institute of Chemical Physics, on C-C and C-N bond formation via C-H activation.

All in all it was a very enjoyable visit to Lanzhou. Our thanks go to Professor Tu for hosting us, Professor Wei Wang and his colleagues for local organisation and to all the speakers.

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 ten most accessed articles in March

This month sees the following articles in Organic & Biomolecular Chemistry that are in the top ten most accessed:

Bioinspired organocatalytic asymmetric reactions
Luca Bernardi, Mariafrancesca Fochi, Mauro Comes Franchini and Alfredo Ricci
Org. Biomol. Chem., 2012, 10, 2911-2922
DOI: 10.1039/C2OB07037E

A convenient approach to ß-heteroarylated (C–N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
M. Bhanuchandra, Malleswara Rao Kuram and Akhila K. Sahoo
Org. Biomol. Chem., 2012, 10, 3538-3555
DOI: 10.1039/C2OB25165E

A seminaphthofluorescein-based fluorescent chemodosimeter for the highly selective detection of cysteine
Xiaofeng Yang, Yixing Guo and Robert M. Strongin
Org. Biomol. Chem., 2012, 10, 2739-2741
DOI: 10.1039/C2OB25178G

On a so-called “kinetic anomeric effect” in chemical glycosylation
Ian Cumpstey
Org. Biomol. Chem., 2012, 10, 2503-2508
DOI: 10.1039/C2OB06696C

A catalytic metal-free Ritter reaction to 3-substituted 3-aminooxindoles
Feng Zhou, Miao Ding and Jian Zhou
Org. Biomol. Chem., 2012, 10, 3178-3181
DOI: 10.1039/C2OB25319D

A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
Jie Chen, Ling Zhou and Ying-Yeung Yeung
Org. Biomol. Chem., 2012, 10, 3808-3811
DOI: 10.1039/C2OB25327E

Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs
Tao Sun, Carl Deutsch and Norbert Krause
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25069A

Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction
Ke-Yin Ye, Li-Xin Dai and Shu-Li You
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB00036A

Silver-promoted Friedel–Crafts reaction: concise total synthesis of (-)-ardeemin, (-)-acetylardeemin and (-)-formylardeemin
Y. Wang, C. Kong, Y. Du, H. Song, D. Zhang and Y. Qin
Org. Biomol. Chem., 2012, 10, 2793-2797
DOI: 10.1039/C2OB00014H

Highly efficient asymmetric anti-Mannich reactions of carbonyl compounds with N-carbamoyl imines catalyzed by amino-thiourea organocatalysts
Jiuzhi Gao, Yongming Chuan, Jiali Li, Fang Xie and Yungui Peng
Org. Biomol. Chem., 2012, 10, 3730-3738
DOI: 10.1039/C2OB00049K

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Organic & Biomolecular Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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)

Issue 19 online with quantum mechanical tunnelling & 2-substituted 3-bromopyrrolidines on the covers

On the front cover is this HOT Emerging Areaarticle from Peter R. Schreiner and co-workers (Justus-Liebig University, Germany) who discuss quantum mechanical tunnelling and provide an overview of the importance of tunnelling in organic chemical reactions.
Discussion includes:

  • a brief history of tunnelling
  • hydrogen tunnelling
  • carbon tunnelling
  • heteroatom tunnelling

Tunnelling control of chemical reactions – the organic chemist’s perspective
David Ley, Dennis Gerbig and Peter R. Schreiner
Org. Biomol. Chem., 2012, 10, 3781-3790
DOI: 10.1039/C2OB07170C

On the inside front cover is this Communication, from Ying-Yeung Yeung and colleagues at National University of Singapore, where a facile and highly enantioselective route to 2-substituted 3-bromopyrrolidines is presented. The authors demonstrate how these can be reached via the bromo-aminocyclisation of 1,2-disubstituted olefinic amides using amino-thiocarbamates as a catalyst. This is also part of our growing Organocatalysis web collection.

A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
Jie Chen, Ling Zhou and Ying-Yeung Yeung
Org. Biomol. Chem., 2012, 10, 3808-3811
DOI: 10.1039/C2OB25327E

Both of these cover articles will be free to access for the next 6 weeks.

Also in this issue:

A perspectiveby Alessandro Massi and Daniele Nanni:
Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications

And 2 HOT articles that are still free to access for another 3 weeks

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid
Mark C. Elliott et al.

Glycosylated diazeniumdiolate-based oleanolic acid derivatives: synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents
Yihua Zhang et al.

View the entire issue HERE, it’s full of lots of great content!

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: Glycosylated diazeniumdiolate-based oleanolic acid derivatives as therapeutic agents for human hepatocellular carcinoma

Following their earlier work on nitric oxide (NO) releasing oleanolic acid (OA) derivatives as therapeutic agents for human hepatocellular carcinoma (HCC) – the third leading cause of cancer death worldwide without effective chemotherapy – Prof. Yihua Zhang and coll. at the Center of Drug Discovery, China Pharmaceutical University (Nanjing, P.R. China) have designed a series of glycosylated diazeniumdiolate derivatives of oleanolic acid.

One of the coupounds has been found to selectively inhibit the proliferation of HCC in vivo but not that of non-tumor liver cells, with relatively low acute toxicity, and may be a promising drug candidate against HCC.

The authors also provide an in-depth analysis of the mechanisms underlying the action of this group of glycosylated diazeniumdiolate-based OA derivatives…

Want to know more? Why not read now, the article will be FREE to access to all for the next four weeks

Glycosylated diazeniumdiolate-based oleanolic acid derivatives: synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents
Zhangjian Huang, Junjie Fu, Ling Liu, Yijun Sun, Yisheng Lai, Hui Ji, Edward E. Knaus, Jide Tian and Yihua Zhang
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25252J, Paper

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)

Foldamer Chemistry web themed issue now published

Here Prof. Ferenc Fülöp, University of Szeged, gives a brief introduction to Organic & Biomolecular Chemistry‘s Foldamer Chemistry web themed issue:

The syntheses and structural and functional investigations of peptide oligomers that adopt designed compact conformations have become challenging tasks in recent decades. β-Amino acids, among them cyclic β-amino acids, find a broad range of use as building blocks for the preparation of modified analogues of biologically active peptides. The peptidomimetic approach in drug research is of significant potential. Since their discovery, the field of foldamers has come of age as a branch of chemistry, and synthetic self-organizing polymers have infiltrated almost all chemical disciplines, either as tools or as topics of fundamental science.

The interest in foldamers originated in the challenge to mimic the structural behaviour of biomolecules with synthetic sequences. This challenge was quickly answered: beautiful structures and programmable self-organization can be achieved with non-natural molecules. Various synthetic methodologies have led to novel building blocks becoming accessible, and a further source of diversity is the combination of different monomer types within a single sequence. Different amino acid homologues can be coupled in specific patterns (α,β-peptides, β,γ-peptides, etc.), all resulting in novel secondary structure patterns. Moreover, the coupling of aromatic building blocks with aliphatic monomers has been achieved, and short βαγ- and βαδ-peptide sequences have recently been described, which points to the practically limitless number of possible combinations. The building-up of higher-order structures from foldamers is a further great challenge and an important trend in the field. The diversity of peptidic foldamers is currently passing through a ramping-up process at all levels.

The present web themed issue covers the syntheses of β-amino acid monomers, and discusses the syntheses, structural investigations and applications of foldamers.

Click here to see all of the articles in the web themed issue

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 paper: Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

In this HOT paper Mark C. Elliott and colleagues at Cardiff University present an investigation on the deprotonation and alkylation of 1-methylcyclohexa-2,5-diene-1-carboxylic acid under a range of conditions. The culmination of the investigation shows that deprotonation of 1-methylcyclohexa-2,5-diene-1-carboxylic acid with n-BuLi in the presence of TMEDA, followed by alkylation, offers a direct and highly diastereoselective route to the corresponding 4-substituted products in which the alkyl group introduced is transto the carboxylic acid.

Mark C. Elliott et al. comment that this result “complements previous findings of H. van Bekkum in which a 4-substituted benzoic acid is reductively alkylated and where, when any selectivity is observed, the alkyl group and the carboxylic acid are preferentially cis.”

Click here for the complete study…..

This HOT article will be FREE TO ACCESS for the next 4 weeks!

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid
Nicholas J. Bennett, Mark C. Elliott, Natalie L. Hewitt, Benson M. Kariuki, Clare A. Morton, Steven A. Raw and Simone Tomasi
Org. Biomol. Chem., 2012
DOI: 10.1039/C2OB25211B

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)

Mannich reactions, carbon nanotubes & polymeric ladderphanes: a taste of what’s to come for Organic & Biomolecular Chemistry’s 10th anniversary issue

Our 10th anniversary themed issue is well under way, with many articles now published online. Here is just a taster of some of the hot articles that are included in the collection so far:

Development of strong Brønsted base catalysis: catalytic direct-type Mannich reactions of non-activated esters via a product-base mechanism
Yasuhiro Yamashita, Hirotsugu Suzuki and Shu Kobayashi
DOI: 10.1039/C2OB25522G

Facile air-oxidation of large aromatic hydrocarbon bay regions to bay region quinones: predicted oxygen-sensitivity of hydrogen-terminated carbon nanotubes
Eric H. Fort and Lawrence T. Scott
DOI: 10.1039/C2OB25208B

Double stranded polymeric ladderphanes with 16-p-electron antiaromatic metallocycle linkers
Hsin-Hua Huang, Chih-Gang Chao, Shern-Long Lee, Hung-Jen Wu, Chun-hsien Chen and Tien-Yau Luh
DOI: 10.1039/C2OB25114K

Solvent and substituent effects on aggregation constants of perylene bisimide p-stacks – a linear free energy relationship analysis
Zhijian Chen, Benjamin Fimmel and Frank Würthner
DOI: 10.1039/C2OB07131B

These 4 HOT artilces will be FREE to access for the next 4 weeks.

There are plenty more articles HERE, covering many different and interesting topics. Why not take a look, we’re sure you’ll find something you will like.

In the weeks to come we will be highlighting more of the hot articles that have been published for our 10th anniversary issue so watch this space!

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 Symposium starts at Shanghai Institute of Organic Chemistry

The 1st Organic & Biomolecular Chemistry International symposium is underway. This event, visiting three prominent organic chemistry departments in China, brings together speakers from China, Europe and North America.

OBC participants

Participants at the OBC Symposium at SIOC

First stop for the symposium was Shanghai Institute of Organic Chemistry, and day was started with an introduction from SIOC Director Professor Kuling Ding. The opening lecture was given by Professor Guo-Qiang Lin, who gave an overview of his work on the synthesis of chiral dienes, useful ligands for transition metal catalysis. Following that OBC Chair Professor Jeffrey Bode (ETH Zurich, Switzerland) presented developments from his group on amide-forming reactions. After the break Professor Dawei Ma (SIOC) showed some of his recent work in the synthesis of the bioactive alkaloids Berbamine and the Communesins.

Professor Dawei Ma presents his research

After lunch Professor Dirk Trauner (LMU Munich, Germany) gave an energetic overview of a number of natural product syntheses, probing reactions beyond the limits of biomimetic synthesis. Next up was Professor Xuhong Qian (East China University of Science and Technology, Shanghai), who gave an overview of his development of dyes for fluorescent sensing and anticancer applications. After coffee Professor Andrei Yudin (University of Toronto) described a number of areas where his group has been using amphoteric molecules, and the day was rounded off by Professor Yong Tang (SIOC) and his work with pendant-bisoxazoline ligands.

Professor Yong Tang speaking at the symposium

Many thanks to all the speakers, chairs and attendees for making this a successful start to the OBC Symposium. Particular thanks go to Professor Shuli You and his colleagues at SIOC for the local organisation of the meeting.

Next stop, Lanzhou….

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)

Nanoscale engineering of wound beds

A collagen-binding peptide with applications in wound healing has been developed by scientists in the US. The peptide is able to invade the strands of collagen, forming a strong and stable non-covalent bond at room temperature. Pendant drug molecules could be attached to the peptide and anchored at the wound site to aid wound healing…

Read the full article at Chemistry World, or read the OBC paper:

Peptides that anneal to natural collagen in vitro and ex vivo
Sayani Chattopadhyay, Christopher J. Murphy, Jonathan F. McAnulty and Ronald T Raines
DOI: 10.1039/C2OB25190F

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)