Synthesis of (-)-Ilimaquinone via a Radical Decarboxylation and Quinone Addition Reaction
Taotao Ling, Erwan Poupon, Erik J. Rueden, and Emmanuel A. Theodorakis*
*Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, Email: etheodorucsd.edu
T. Ling, E. Poupon, E. J. Rueden, E. A. Theadorakis, Org. Lett., 2002, 4, 819-822.
DOI: 10.1021/ol025501z (free Supporting Information)
The stereoselective synthesis of (-)-ilimaquinone is based on a radical decarboxylation and quinone addition methodology that produces a quinone derivative from reaction of thiohydroxamic acid derivative with benzoquinone. Final functionalization of this intermediate to ilimaquinone is achieved by exploring the electronic effects of the residual thiopyridyl group.
Radical decarboxylation and quinone addition: