AI Article Synopsis
- The study focuses on the transformation of trans-4-Hydroxy-L-proline into a tricyclic compound that mimics three connected rings found in the anticancer antibiotic MPC1001.
- The new tricyclic model includes key structural features, such as dihydrooxepin and diketopiperazine subunits, and incorporates one sulfur atom from the natural antibiotic.
- A novel method was developed for creating the diketopiperazine unit through enolate cyclization with a phenyl carbamate, while the dihydrooxepin ring was synthesized using acid-induced cyclization techniques.
Article Abstract
trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine subunits, as well as one of the sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.
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| http://dx.doi.org/10.1021/jo802344t | DOI Listing |
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