AI Article Synopsis
- The synthesis of (±)-minfiensine, a Strychnos alkaloid, was accomplished using a series of chemical reactions including an intramolecular amidofuran Diels-Alder cycloaddition.
- This process allowed for efficient creation of the complex core structure of the alkaloid through a domino reaction sequence.
- The final steps involved a palladium-catalyzed reaction to successfully build the last ring, completing the synthesis of (±)-minfiensine in high yield.
Article Abstract
The total synthesis of the Strychnos alkaloid (±)-minfiensine was achieved via an intramolecular amidofuran Diels-Alder cycloaddition/rearrangement followed by an iminium ion/cyclization cascade sequence. This domino process provides for a rapid access to the unique 1,2,3,4-tetrahydro-9a,4a-iminoethanocarbazole core structure found in the alkaloid minfiensine (2). In this paper, the full account of our synthetic study is described, highlighting the successful application of the cascade sequence to form the A/B/C/D rings of (±)-minfiensine (2) in high yield. A palladium-catalyzed enolate coupling reaction was then used to furnish the final E ring and complete the total synthesis of (±)-minfiensine (2).
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| http://dx.doi.org/10.1021/acs.joc.6b00771 | DOI Listing |
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