[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products

Among the fundamental chemical transformations in organic synthesis, the [3,3]-sigmatropic rearrangement occupies a unique position as a powerful, reliable, and well-defined method for the stereoselective construction of carbon-carbon or carbon-heteroatom bonds. While many other reactions can unite...

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Bibliographic Details
Published in:Chemical Society reviews 2009-11, Vol.38 (11), p.3133-3148
Main Authors: Ilardi, Elizabeth A, Stivala, Craig E, Zakarian, Armen
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Methods
Organic Chemistry Phenomena
Stereoisomerism
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Summary:Among the fundamental chemical transformations in organic synthesis, the [3,3]-sigmatropic rearrangement occupies a unique position as a powerful, reliable, and well-defined method for the stereoselective construction of carbon-carbon or carbon-heteroatom bonds. While many other reactions can unite two subunits and create a new bond, the strengths of sigmatropic rearrangements derive from their ability to enable structural reorganization with unmatched build-up of complexity. Recent applications that illustrate [3,3]-sigmatropic processes as a key concept in the synthesis of complex natural products are described in this tutorial review, covering literature from about 2001 through early 2009.
ISSN:0306-0012
1460-4744
DOI:10.1039/b901177n