Disconnections must correspond to known, reliable reactions
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص695
2025-07-10
609
The chemists who first made amelfolide chose to make it from an amine and an acyl chloride because they knew that this reaction, a standard way of making an amide, had a very good chance of success. They chose to disconnect the C–N bond because this disconnection corresponds to a reliable reaction in a way that no other possible disconnection of this molecule does. Now that you’ve seen the principle of retrosynthetic analysis at work, you should be able to suggest a reasonable disconnection of the compound in the margin, known as daminozide. You probably spotted immediately that daminozide is again an amide, so the best disconnecttion is the C–N bond, which could take us back to acyl chloride and dimethylhydrazine. This time we’ve written ‘C–N amide’ above the retrosynthetic arrow as a reminder of why we’ve made the disconnection and we advise you to follow this practice.
Now, in fact, there is a problem with this acyl chloride—it would be unstable as it can cyclize to an anhydride. But this poses no problem for the synthesis of daminozide—we could just use the anhydride instead, since the reaction should be just as reliable. A better retrosynthesis therefore gives the anhydride and indeed this is how daminozide is made.
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