Organic & Biomolecular Chemistry Blog

Hans-Joachim Knölkner and colleagues reveal the link between this beautiful church in Dresden and β-isocomene: silicon

Find out more about this curious conection in this article and read about the total synthesis of the sesquiterpenes (±)-β-isocomene and (±)-isocomene via a Lewis acid promoted [3 + 2] cycloaddition of allyl-tert-butyldiphenylsilane.

This article will be free to access until 10th November

Organosilicon-mediated total synthesis of the triquinane sesquiterpenes (±)-β-isocomene and (±)-isocomene
Arndt W. Schmidt, Thomas Olpp, Elke Baum, Tina Stiffel and Hans-Joachim Knölker
Org. Biomol. Chem., 2010, 8, 4562-4568
DOI: 10.1039/C0OB00051E

This colourful and arty cover by Chunling Fu, Shengming Ma and colleagues shows the mechanism of a highly regio- and stereo- selective hydration of 1,2-allenylic sulfoxides.

In this reaction, the proton acts as the electrophile and water coming from the solvent attacks the sulfinyl group.
Not convinced yet?  There are even crystal structures to prove it!

Download the article for free until 10th November

Studies on highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides
Zhao Fang, Chao Zhou, Chunling Fu and Shengming Ma
Org. Biomol. Chem., 2010, 8, 4554-4561
DOI: 10.1039/C0OB00007H

Ulrik Gether, Kristian Stromgaard and colleagues at University of Copenhagen explore the structure-activity relationships of the first small molecule inhibitor of PICK 1, a potential drug target against brain ischemia, pain and cocain addiction.

It is the inside cover of OBC Issue 19 and it will be free to access until October 19th.

Read it and try to PICK 1 comment!

Structure–activity relationships of a small-molecule inhibitor of the PDZ domain of PICK1
Anders Bach, Nicolai Stuhr-Hansen, Thor S. Thorsen, Nicolai Bork, Irina S. Moreira, Karla Frydenvang, Shahrokh Padrah, S. Brøgger Christensen, Kenneth L. Madsen, Harel Weinstein, Ulrik Gether and Kristian Strømgaard
Org. Biomol. Chem., 2010, 8, 4281-4288
DOI: 10.1039/C0OB00025F

Dan Pantos and co-workers at Cambridge University explore the ‘sergeants and soldiers’ behaviour where a chiral derivative, amino acid derivatives of naphtalene-diimides (NDIs), imposes its chirality on a structure formed out of achiral derivatives.

Supramolecular systems, nanotubes, C₆₀… everything included in this very interesting paper, front cover of OBC Issue 19.

Reading it is a must (although not an order!) and commenting on it an option
Free to access until 19th October

The sergeants-and-soldiers effect: chiral amplification in naphthalenediimide nanotubes
Tom W. Anderson, Jeremy K. M. Sanders and G. Dan Pantoş
Org. Biomol. Chem., 2010, 8, 4274-4280
DOI: 10.1039/C0OB00027B

Thomas Nugent and co-workers talk about the top organocatalysts for cyclic ketones and discover a 2-picolylamine template which is a promising new organocatalyst for aqueous aldol reactions.

Do you want to read more? You can do it for free until early October here!

Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions
Thomas C. Nugent, M. Naveed Umar and Ahtaram Bibi
Org. Biomol. Chem., 2010, 8, 4085-4089
DOI: 10.1039/C0OB00049C

Isao Kii, Takamitsu Hosoya and colleagues modify an azido-biomolecule by a new method that conjugates three molecules spontaneously in a catalyst-free strain-promoted “double-click” (SPDC) reaction.

If you find “click chemistry” interesting, this will double your enjoyment!

Discover this facile method to prepare various functional biomolecules by “clicking” here.

Strain-promoted double-click reaction for chemical modification of azido-biomolecules
Isao Kii, Akira Shiraishi, Toshiyuki Hiramatsu, Takeshi Matsushita, Hidehiro Uekusa, Suguru Yoshida, Makoto Yamamoto, Akira Kudo, Masatoshi Hagiwara and Takamitsu Hosoya
Org. Biomol. Chem., 2010, 8, 4051-4055
DOI: 10.1039/C0OB00003E , Communication

Free to access until early October!

What do you think?

Jian Zhou and colleagues at East China Normal University in Shanghai find a very straightforward method for the synthesis of oxindole, a very important subunit in many bioactive natural products and drugs.

OBC cover of Issue 17 shows the direct road that leads to the synthesis of this very useful product. It is free to access for 6 weeks from publication of the issue.

Do you want to know more? Read it here and let us know what you think!

A facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reaction
Yun-Lin Liu, Feng Zhou, Jun-Jie Cao, Cong-Bin Ji, Miao Ding and Jian Zhou
Org. Biomol. Chem., 2010, 8, 3847-3850