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

2009; Royal Society of Chemistry; Volume: 38; Issue: 11 Linguagem: Inglês

10.1039/b901177n

1460-4744

Elizabeth A. Ilardi, Craig E. Stivala, Armen Zakarian,

Oxidative Organic Chemistry Reactions

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.