Synthesis of 6-functionalized tricyclodecadienones using Barton's radical decarboxylation reaction. Generation of tricyclo[5.2.1.0^2,6]decatrienone, a norbornene annulated cyclopentadienone

Jie Zhu, Antonius J. H. Klunder and Binne Zwanenburg*

*Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525 ED, Nijmegen, The Netherlands

J. Zhu, A. J. H. Klunder, B. Zwanenburg, Tetrahedron, 1995, 51, 5099-5116.

DOI: 10.1016/0040-4020(95)98707-O

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Abstract

An effective synthesis of 6-functionalized endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-ones starting from carboxylic acid has been accomplished whereby the chemical scope of the tricyclodecadienone system as a synthetic equivalent of cyclopentadienone has been expanded.

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reaction pathway

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reprinted with permission from Elsevier

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Key Words

Barton Decarboxylation, Diels-Alder Reaction

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ID: J72-Y1995-280