Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
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Authors: | Szil rd Varga,P ter Angyal,G bor Martin,Orsolya Egyed,Tam s Holczbauer,Tibor So s |
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Affiliation: | Szilárd Varga,Péter Angyal,Gábor Martin,Orsolya Egyed,Tamás Holczbauer,Tibor Soós |
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Abstract: | We report 8‐step syntheses of (?)‐minovincine and (?)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transformations included organocatalytic Michael‐aldol condensation, a multistep anionic Michael‐SN2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo‐ and regioselective transformations. |
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Keywords: | alkaloids asymmetric catalysis biomimetic synthesis organocatalysis total synthesis |
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