AI Article Synopsis
- - A highly selective total synthesis of (-)-jimenezin, an effective anticancer compound, was achieved using a process called sequential intramolecular amide enolate alkylation (IAEA).
- - The research focused on understanding why the second IAEA step produced such high stereoselectivity when creating a flexible tetrahydrofuran structure.
- - It was found that the presence of an oxygen atom in the neighboring tetrahydropyran ring plays a key role in achieving perfect stereocontrol during this synthesis step.
Article Abstract
A highly stereoselective asymmetric total synthesis of (-)-jimenezin (), a potent anticancer acetogenin, was efficiently completed with the key feature being a sequential intramolecular amide enolate alkylation (IAEA). Our investigation to probe the origin of the complete stereoselectivity in the second IAEA step to form the conformationally flexible tetrahydrofuran with perfect stereocontrol identified the presence of the oxygen atom in the adjacent tetrahydropyran ring to be crucial.
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| http://dx.doi.org/10.1021/acs.orglett.2c00196 | DOI Listing |
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