Naturalproductman’s Blog

Hey, is that a natural product?!

C-C bond breaking mechanism

Posted by naturalproductman on November 8, 2012

Here’s an interesting paper where the authors used 18O2 to label one of the oxygens found in the product to investigate the mechanism. Now I’m going to be a little bit critical here but in the supporting information they put the 18O-label on the carbonyl oxygen but in the manuscript they don’t know if it is on the O-benzyl of the ester or the carbonyl oxygen. Moreover the abstract figure shows that the 18O is on the carbonyl oxygen but they really don’t know. It’s a bit deceiving in the paper because it kind of sounds like they determined it through GC-MS but in the supporting information I could not find the GC-MS trace. I guess there is a limitation in analytical technology to determine the position of the 18O. But still it is not clear from the paper that they don’t know which position the 18-oxygen is.

O

ACIE paper

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