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Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions
Author(s) -
Varga Szilárd,
Angyal Péter,
Martin Gábor,
Egyed Orsolya,
Holczbauer Tamás,
Soós Tibor
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202004769
Subject(s) - cascade , steric effects , regioselectivity , aldol reaction , reagent , combinatorial chemistry , chemistry , sequence (biology) , aldol condensation , cascade reaction , catalysis , organic chemistry , stereochemistry , chromatography , biochemistry
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 N 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.