Flipping through C&EN brought my attention to a recent review published in Angewandte Chemie (DOI:10.1002/anie.200601551) about the history of quinine synthesis. If you like (somewhat lengthy) stories about the history of chemistry and natural product synthesis, you might want to print this one out for bedtime reading. And don't forget to drink a gin and tonic now and then to keep the malaria away! C!
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Mmmm Gin and Tonic - old trusted friend. I have consumed endless quantities of this stuff over the years despite the fact that Malaria can't be considered a major problem in Denmark. But just to be on the safe side I recommend a couple of GTs with a twist of lime on a weekly basis. Quinine is fluorescent as hell and in autumn in Denmark when the sun is about to set your GT will actually get an eerie light blue colour. Has anyone else observed this or have I just been seeing things in my intoxicated state? D!
I have a mechanism related question. What is the mechanism for the conversion of a primary alcohol to an alkyl iodide using triphenylphosphine, iodine and imidazole?
Cheers,
Sam
Well Sam I fail to see the connection with gin and tonic but I have an idea how this works and I quite like the reaction due to the nature og one of the intermediates. However, you'll have to think about it yourself. The key to a reaction of this type is that you are eventually going to end up with some triphenylphosphine oxide (TPPO). To achive this your alcohol need to do a nucelophilic attack on "a phosphorus species" to generate a leaving group (ie. TPPO) that can be displaced by iodide. Now the first thing you have to figure out is the nature of the electrophilic phosphorus species. Triphenylphosphine is an excellent nucleophile and iodine is a good electrophile - try combining these two fellas to generate an electrophilic phosphonium salt (this is the intermediate I like) and see where that gets you. D!
Hjælper det
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