Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and Diynes

Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and Diynes

The total syntheses of (−)-herbindoles A, B, and C as naturally occurring forms were accomplished for the first time through transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes. This strategy provided a highly efficient synthetic route to all three herbindole...

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Veröffentlicht in:Organic letters 2012-04, Vol.14 (7), p.1914-1917
Hauptverfasser: Saito, Nozomi, Ichimaru, Taisuke, Sato, Yoshihiro
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Cyclization
Diynes - chemistry
Indole Alkaloids
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Porifera - chemistry
Stereoisomerism
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Zusammenfassung:The total syntheses of (−)-herbindoles A, B, and C as naturally occurring forms were accomplished for the first time through transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes. This strategy provided a highly efficient synthetic route to all three herbindoles from an identical indoline derivative as a common intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300571b