Total Synthesis of (−)‑N‑Methylwelwitindolinone C Isothiocyanate Based on a Pd-Catalyzed Tandem Enolate Coupling Strategy

Total Synthesis of (−)‑N‑Methylwelwitindolinone C Isothiocyanate Based on a Pd-Catalyzed Tandem Enolate Coupling Strategy

The highly stereocontrolled total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate is described, which features the expeditious construction of a bicyclo[4.3.1]­decane ring system by a palladium-catalyzed tandem enolate allylation/arylation reaction.

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Veröffentlicht in:Organic letters 2015-08, Vol.17 (15), p.3918-3921
Hauptverfasser: Komine, Keita, Nomura, Yusuke, Ishihara, Jun, Hatakeyama, Susumi
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyanobacteria - chemistry
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
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Zusammenfassung:The highly stereocontrolled total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate is described, which features the expeditious construction of a bicyclo[4.3.1]­decane ring system by a palladium-catalyzed tandem enolate allylation/arylation reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01952