Lyconadin A
31 July 2009
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5 Comments
Latest piece for the RSC in Chemistry World. A bit cheeky – I promised a new post, but that’ll have to wait a day or two. I have been busy though – have a look here too, at an interview about the NaH debate.
(6 votes, average: 3.67 out of 5)
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nice article.
liked the interview.
in my opinion this might induce a historical change in the chemical community. with fair and sophisticated public criticism like this, science will really profit.
Docherty says: ‘To confirm the results will take a more methodological approach, but our initial collaborative studies suggest that in scrupulously anaerobic conditions, no oxidation reaction occurs, suggesting that atmospheric or adsorbed oxygen is somewhat critical to the chemistry. I have no doubt that their chemistry works, but a thorough examination of the conditions, along with a more-varied substrate screen seem crucial to understanding this exciting science. It’s a shame they didn’t do this before publishing this communication.’
The American Chemical Society, which publishes JACS, was contacted by Chemistry World but has yet to comment on the episode.
I think this will set a hysteric precedent: one day we will be telling to our grand-grand-clones that we were there when it happened. And by the way, Dr. Docherty finished publishing in the ACS journals already. As you are aware, expressing a constructive criticism can be healthy in moderation but he is really pushing it.
Wow.. This synthesis is quite amazing.
I absolutely love the the CBS reduction followed by the pd/c reduction. That requires some pretty serious guts… Hydrogenations all most never quite work out how you want them to…
Nice interview, indeed!
“[...]Wang initially remained adamant that something unusual is happening in the reaction, but later appeared to accept that oxygen may play a role. The following day he added: ‘Since we didn’t run the reaction in a drybox, i.e. an absolutely inert atmosphere, it is also likely that NaH plus trace amount of air did the oxidations through radical-type mechanism.[...]”
Oxygen MAY play a role? WTF?!? This reaction does NOT work with ppm amounts of oxygen. This has to be stoichiometric…
I agree that the CBS-pd/c sequence is pretty interesting. However, that ketone gets reduced and reoxidized a couple of times during the synthesis which seems a tad inelegant.