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Elatenyne, or When Natural Products Turn Bad…   

9 October 2006 5,040 views 5 Comments

elatenyne.jpg

Burton, Sheldrake and Jamieson. ACIEE, 2006, Early View. DOI: 10.1002/anie.200602211.

I don’t want to blow our trumpet excessively, but we (that is the Burton group) have just published an Angewandte about total synthesis and structural reassignment of natural products. It’s based upon “elatenyne”, which we made, but it turns out that the NMR data of the synthetic sample didn’t match the biological sample. A bit of investigating has shown that perhaps the whole series has been incorrectly assigned…

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5 Comments

  • milkshake says:

    The consolation is that the real re-assigned elatenyne will be much easier to make – and one can start all over from the very same bislactone :)

  • KP Worrell says:

    So is there any reason that the natural products people who announced the structure couldn’t get an x-ray of it? It doesn’t look like it would have been impossible to do so.

  • Tot. Syn. says:

    How can anyone know whether or not a compound will be crystalline? Certainly, the intermediates in my own work are entirely unpredictable. One can propose that a certain compound looks like it might be solid, but never be sure.

  • Chemist of Sorts says:

    People rely way too much on X-ray; it has become a knee jerk response for many to unknown structures. Careful NMR work is just as reliable and doesn’t require crystaline compounds. The main exceptions are for large complex systems with numerous stereocenters. The paper cited here also shows a nice exception when some compounds are expected to have virtually identical NMR data. I have heard too many people say, to paraphrase ‘I can’t get a crystal, so I can’t solve the structure’. X-ray is a nice tool, but realize that it is just one tool among many and not a cure-all.

  • Hap says:

    …and Diazonamide A was a case where the X-ray structure was less than clear, so it’s possible that even if you get a crystal structure, you may not have the correct structure. In addition, with some compounds, functionalization with a pendant group (for those needing a heavy atom or a chiral group for absolute stereo) may cause rearrangement.

    There is also a recent KCN/Snyder review (ACIE 44, p.1012) that has lots of structures where the original assignment was wrong.