AI Article Synopsis
- 4-Hydroxy-L-proline was transformed into a specialized ring system, known as tetrahydrooxepino[4,3-b]pyrrole, which is part of the antitumor drug MPC1001.
- Key reactions included creating a vinylogous amide using Bredereck's reagent and then cyclizing this compound into a seven-membered oxacyclic structure through an acid-induced reaction.
- This process highlights essential synthetic techniques in organic chemistry for developing potent pharmaceuticals.
Article Abstract
4-Hydroxy-L-proline was converted into the tetrahydrooxepino[4,3-b]pyrrole ring system characteristic of the potent antitumor agent MPC1001. Key steps were regioselective formation of a vinylogous amide by use of Bredereck's reagent and acid-induced cyclization of an alcohol onto the carbon-carbon double bond of that amide by addition-elimination to generate the seven-membered oxacyclic subunit.
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| http://dx.doi.org/10.1021/ol071147z | DOI Listing |
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