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

Chem Soc Rev. 2009 Nov;38(11):3133-48. doi: 10.1039/b901177n. Epub 2009 Sep 2.

Abstract

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.

Publication types

  • Review

MeSH terms

  • Biological Products / chemical synthesis*
  • Methods
  • Organic Chemistry Phenomena*
  • Stereoisomerism

Substances

  • Biological Products