A [4+4] annulation strategy for the synthesis of eight-membered carbocycles based on intramolecular cycloadditions of conjugated enynes
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Danheiser_A 4+4 annulation.pdf
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Author(s)
Robinson, Julia M.
Tlais, Sami F.
Fong, Jennie
Danheiser, Rick Lane
Date Issued
September 2011
Journal
Tetrahedron
Publisher
Elsevier
Citation
Robinson, Julia M., Sami F. Tlais, Jennie Fong, and Rick L. Danheiser. “A [4+4] Annulation Strategy for the Synthesis of Eight-Membered Carbocycles Based on Intramolecular Cycloadditions of Conjugated Enynes.” Tetrahedron 67, no. 51 (December 2011): 9890–9898.
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Author's final manuscript
Abstract
A [4+4] annulation strategy for the synthesis of eight-membered carbocycles is reported that proceeds via a cascade involving two pericyclic processes. In the first step, the [4+2] cycloaddition of a conjugated enyne with an electron-deficient cyclobutene generates a strained six-membered cyclic allene that isomerizes to the corresponding 1,3-cyclohexadiene. In the second step, this bicyclo[4.2.0]octa-2,4-diene intermediate undergoes thermal or acid-promoted 6-electron electrocyclic ring opening to furnish a 2,4,6-cyclooctatrienone. The latter transformation represents the first example of the promotion of 6-electron electrocyclic ring opening reactions by acid.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1016/j.tet.2011.09.031
