B.R.S.M. To strive, to seek, to find and not to give a yield


Named Reactions 2: Break It Down Now

Physics Nobel Laureate, legendary teacher and all-round cool guy Richard Feynman once said: “[There’s a] difference between knowing the name of something and knowing something”. This is true in a whole range of fields, and we’ve probably all seen enough students confidently assert that a particular step is “just a simple named reaction”, only to completely crumble when asked the mechanism or conditions. Still, I think named reactions are a great way of learning some really important chemistry that can then be applied to many other things. A chemist who knows, say, the fifty most common named reactions and a decent chunk of basic theory will be in a good position to take a guess at the mechanism of most things they encounter.  They're also a useful conversational shorthand if you want to convey how something works without reaching for a pen and paper. Very few reactions are so obscure and ‘out there’ that they’re not at least conceptually related to things we all know well. For example, I set this as part of a group problem session I ran last week:[1]

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Kibdelone C

Porco et al., J. Am. Chem. Soc., 2011, Article ASAP; [PDF] [SI] [GROUP]

DOI: 10.1021/ja203642n

Ready et al., J. Am. Chem. Soc., 2011, Article ASAP; [PDF] [SI] [GROUP]

DOI: 10.1021/ja204040k

Here’s an odd occurrence; two quite different syntheses of the natural product kibdelone C in appeared in the JACS ASAP on the same day last week; one by the Porco group and another by Ready and coworkers. Each acknowledges the other for sharing details of the work before publication, so I guess the authors were less surprised than I was. There are a number of kibdelones, all of which are quite similar and tend to interconvert on standing. They boast antibacterial, antinematodal and anticancer activity. The mode of action isn’t known, but they look likely to bind nucleic acids.

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