Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions
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- Szilárd Varga
- Institute of Organic Chemistry Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
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- Péter Angyal
- Institute of Organic Chemistry Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
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- Gábor Martin
- Institute of Organic Chemistry Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
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- Orsolya Egyed
- Instrumentation Center Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
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- Tamás Holczbauer
- Institute of Organic Chemistry Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
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- Tibor Soós
- Institute of Organic Chemistry Research Centre for Natural Sciences 2 Magyar tudósok krt. 1117 Budapest Hungary
抄録
<jats:title>Abstract</jats:title><jats:p>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‐S<jats:sub>N</jats:sub>2 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.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 59 (32), 13547-13551, 2020-06-03
Wiley