Nature Protocols | Stepwise

Themes from the 22nd International Symposium: Synthesis in Organic Chemistry

Having left my meticulously drawn maps and notes on the dining room table, I boldly set off to Cambridge for the Synthesis in Organic Chemistry Symposium. I was immediately confronted by three Universal Laws:

1. If a bed-and-breakfast is within a 100 m radius of a person’s home, said person is unlikely to know of its existence.

2. People driving swish cars seldom know the directions to the nearest train station (or anything else regarding public transport).

3. Turning right instead of left can have consequences significantly exceeding the ease with which the mistake can be made.

Despite these obstacles, I found Vine Farm, and later the train station, the important bus stops, and Churchill College itself.

After a moderately sunny weekend, the days of the conference were cold, overcast and windy: perfect weather to take shelter in a lecture theatre and escape into the wonderful world of organic synthesis. I was pleasantly surprised to find that I understood enough of the chemistry to follow most of the talks and found myself wishing that I could be in the lab again.

Themes that emerged, at least in my own mind, were:

1. Flow Chemistry and Automated Synthesis.

Steven Ley has developed many flow chemistry methods, and talked about using these systems for reactions where the method has already been optimised and where a compound needs to be prepared in bulk, to allow the valuable minds and skills of PhD students and post-docs to concentrate on new reactions. Vapourtec had a stand to demonstrate their instruments plus an impressive list of publications where their machines had been used many of which had Steve Ley’s name in the author list.

The ReactIR Flow Cell was also mentioned in Helma Wennemers talk in the context of looking at reaction mechanisms.

Peter Seeberger also talked about automated synthesis, this time for the synthesis of oligosaccharides in an approach analogous to that of automated peptide synthesis. His protocol Continuous-flow reactor-based synthesis of carbohydrate and dihydrolipoic acid-capped quantum dots is being published on our site this week.

2. Emergence of kits to perform catalytic reactions.

Prof. Buchwald spoke about the palladium-catalyzed cross coupling reactions that his group has developed and studied, revealed how the ligand names were derived (named after labmembers (e.g. BrettPhos after Brett Fors) and his cats (e.g. RuPhos after Rufus)) and that he was working with Aldrich and STREM to provide the catalyst reagents in kit form.

Both STREM and another company, Johnson Matthey Catalysts had stands at the conference. Johnson Matthey Catalysts provide kits for performing a range of reactions, including those catalysed by enzymes.

3. The pervasive use of SciFinder.

SciFinder was in fact mentioned in the very first talk by Larry Overman, and quite often in conversation during the course of the conference. It is affiliated with the American Chemical Society and I gather that it was a database containing metadata for chemistry-related articles – similar in a way to PubMed, but with more functionality (including the ability to search by chemical structure) and a price-tag. I was relieved to find that Nature Protocols was present in the database!

4. The Holy Grail of 100 % ee

Unsurprisingly, almost all of the compounds-of-interest were chiral, and their successful synthesis required developing enantioselective reactions. Helma Wennemers, for example, talked about her work on developing catalysts that are based on the chemistry of the active sites of enzymes.

And Finally

While all of the talks were excellent, the one that was most memorable was Eiichi Nakamura’s “Imaging of Single Organic Molecules in Motion”. I am not sure how I managed to miss the publication of the original papers, but watching the electron microscopy videos of molecules wiggling through or on top of nanotubes was very pleasing indeed (see also this JACS image challenge).

Alkenyl fullerene in a carbon nanotube

And the most entertaining talk – which included various magic tricks! – was that given by David Leigh on “Making the tiniest machines”. The machines he described were based on catenanes and rotaxanes, which are both examples of interlocked molecules. Again, I am not sure what rock I was trapped under not to notice the original publications, but these images might whet your appetitie if you also somehow managed to miss them.

from A synthetic small molecule that can walk down a track_

from A molecular information ratchet_

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