AI Article Synopsis
- A new theory proposes that latrunculin A, a natural compound, may transform into a new compound called thiopyrone CTP-431 when stored in methanol for a long time.
- The process involves the opening of latrunculin A's hemiacetal, leading to a series of chemical reactions, including dehydration and an intramolecular Diels-Alder reaction.
- Evidence is provided to support the idea that the rearrangement from thiazolidinone to thiopyrone can actually happen experimentally.
Article Abstract
An intriguing hypothesis that latrunculin A, a well-known natural product, might have undergone transformation into the unprecedented thiopyrone CTP-431 upon long-term storage in methanol is advanced. Thus, opening of the hemiacetal of latrunculin A, followed by E1CB elimination, and dehydration would give a polyene that could undergo intramolecular Diels-Alder reaction, followed by methanolysis of the thiazolidinone ring and ring closure by intramolecular thiol addition to an enone. Experimental evidence that the novel thiazolidinone to thiopyrone rearrangement can occur is presented.
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| http://dx.doi.org/10.1021/acs.joc.8b01258 | DOI Listing |
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