[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...

Full description

Saved in:
Bibliographic Details
Published inChemical Society reviews Vol. 38; no. 11; pp. 3133 - 3148
Main Authors Ilardi, Elizabeth A, Stivala, Craig E, Zakarian, Armen
Format Journal Article
LanguageEnglish
Published England 01.11.2009
Subjects
Biological Products - chemical synthesis
Methods
Organic Chemistry Phenomena
Stereoisomerism
Online AccessGet full text

Cover

More Information
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.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-3
content type line 23
ObjectType-Review-1
ISSN:0306-0012
1460-4744
DOI:10.1039/b901177n