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- Title
Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions.
- Authors
Varga, Szilárd; Angyal, Péter; Martin, Gábor; Egyed, Orsolya; Holczbauer, Tamás; Soós, Tibor
- 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.
- Subjects
MANNICH reaction; CATALYSTS; BIOMIMETIC synthesis; CATALYSIS; CONDENSATION
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 32, p13649
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202004769