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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creator	Saito, Nozomi Ichimaru, Taisuke Sato, Yoshihiro
description	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.
doi_str_mv	10.1021/ol300571b
format	Article
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subjects	Animals Biological Products - chemical synthesis Biological Products - chemistry Catalysis Cyclization Diynes - chemistry Indole Alkaloids Indoles - chemical synthesis Indoles - chemistry Molecular Structure Porifera - chemistry Stereoisomerism
title	Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and Diynes
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