Total Synthesis of (−)-Strychnine via the Wieland-Gumlich Aldehyde

Total Synthesis of (−)-Strychnine via the Wieland-Gumlich Aldehyde

Fifteen steps suffice for an enantioselective total synthesis of (−)‐strychnine (1) from 1,3‐cyclohexanedione. The key steps are the easy generation of the enantiopure intermediate 2, the closure of the piperidine ring by a reductive Heck reaction, and the elaboration of the indoline nucleus in an a...

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Veröffentlicht in:Angewandte Chemie International Edition 1999-02, Vol.38 (3), p.395-397
Hauptverfasser: Solé, Daniel, Bonjoch, Josep, García-Rubio, Silvina, Peidró, Emma, Bosch, Joan
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids
Asymmetric synthesis
Nitrogen heterocycles
Palladium
Total synthesis
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Zusammenfassung:Fifteen steps suffice for an enantioselective total synthesis of (−)‐strychnine (1) from 1,3‐cyclohexanedione. The key steps are the easy generation of the enantiopure intermediate 2, the closure of the piperidine ring by a reductive Heck reaction, and the elaboration of the indoline nucleus in an advanced synthetic stage. TBDMS=tert‐butyldimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5