Total Synthesis of Pinnatoxin A

A familiar ring: A ruthenium‐catalyzed cycloisomerization of an enyne, synthesized by an exo‐selective Diels–Alder reaction with an α‐methylene lactone as the dienophile, proved to be highly effective for the construction of the 27‐membered carbocycle of pinnatoxin A. The total synthesis was complet...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (37), p.7091-7094
Main Authors: Nakamura, Seiichi, Kikuchi, Fumiaki, Hashimoto, Shunichi
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Cyclization
cycloaddition
macrocycles
natural products
ruthenium
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
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Summary:A familiar ring: A ruthenium‐catalyzed cycloisomerization of an enyne, synthesized by an exo‐selective Diels–Alder reaction with an α‐methylene lactone as the dienophile, proved to be highly effective for the construction of the 27‐membered carbocycle of pinnatoxin A. The total synthesis was completed upon the formation of the seven‐membered cyclic imine by self‐catalyzed dehydration.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802729