Metathesis Reactions in Total Synthesis

With the exception of palladium‐catalyzed cross‐couplings, no other group of reactions has had such a profound impact on the formation of carbon–carbon bonds and the art of total synthesis in the last quarter of a century than the metathesis reactions of olefins, enynes, and alkynes. Herein, we high...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-07, Vol.44 (29), p.4490-4527
Main Authors: Nicolaou, K. C., Bulger, Paul G., Sarlah, David
Format: Article
Language:English
Subjects:
alkene metathesis
Alkenes - chemistry
Alkylation
alkyne metathesis
Alkynes - chemistry
Carbon - chemistry
Catalysis
Chemistry, Organic - methods
Cyclization
enyne metathesis
Models, Chemical
natural products
Organometallic Compounds - chemical synthesis
Palladium - chemistry
Stereoisomerism
total synthesis
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Summary:With the exception of palladium‐catalyzed cross‐couplings, no other group of reactions has had such a profound impact on the formation of carbon–carbon bonds and the art of total synthesis in the last quarter of a century than the metathesis reactions of olefins, enynes, and alkynes. Herein, we highlight a number of selected examples of total syntheses in which such processes played a crucial role and which imparted to these endeavors certain elements of novelty, elegance, and efficiency. Judging from their short but impressive history, the influence of these reactions in chemical synthesis is destined to increase. The benefits of metathesis reactions (alkene, enyne, and alkyne) are made apparent in this stimulating Review article. The authors highlight a number of total syntheses featuring these important carbon–carbon bond‐forming reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500369