A Synthesis of Echinopine B

In a short synthesis of echinopine B, a guaiane‐like intermediate was generated through a methylenecyclopentane annulation onto a substituted cycloheptenone. The resulting bicyclic compound was converted into the natural product by a PtCl2‐catalyzed enyne cycloisomerization (see scheme). Several lat...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-07, Vol.51 (30), p.7572-7576
Hauptverfasser:	Michels, Theo D., Dowling, Matthew S., Vanderwal, Christopher D.
Format:	Artikel
Sprache:	eng
Schlagworte:	annulation Biological Products - chemical synthesis Biological Products - chemistry Cyclization Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Echinops Plant - chemistry enyne cycloisomerization homogeneous catalysis Isomerism rearrangement sesquiterpenes Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry
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Beschreibung
Zusammenfassung:	In a short synthesis of echinopine B, a guaiane‐like intermediate was generated through a methylenecyclopentane annulation onto a substituted cycloheptenone. The resulting bicyclic compound was converted into the natural product by a PtCl2‐catalyzed enyne cycloisomerization (see scheme). Several late‐stage polycyclic rearrangement products were isolated and characterized.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201203147