[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 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.
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106, USA.
Elizabeth A
EA
Ilardi
Craig E
CE
Stivala
Armen
A
Zakarian
D001688:Biological Products / Q000138:chemical synthesis*; D008722:Methods; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism
D001688:Biological Products