- IMDAF Cascade Approach toward the Synthesis of the Alkaloid (±)-Minfiensine
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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).
- Leverett, Carolyn A.,Li, Gang,France, Stefan,Padwa, Albert
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p. 10193 - 10203
(2016/11/17)
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- Intramolecular Diels-Alder cycloaddition/rearrangement cascade of an amidofuran derivative for the synthesis of (±)-minfiensine
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An efficient synthesis of (±)-minfiensine has been accomplished employing an intramolecular Diels-Alder cycloaddition/rearrangement cascade of an amidofuran derivative. Thermal reorganization of the initially formed [4 + 2]-cycloadduct affords the critica
- Li, Gang,Padwa, Albert
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p. 3767 - 3769
(2011/09/30)
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