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Communication | Regular issue | Vol 31, No. 6, 1990, pp.971-976
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5342
The Birch Reduction/Alkylation of Phthalides. The Synthesis of Some Substituted Bicyclo[3.2.1]octanes

Vernon G. S. Box* and George P. Yiannikouros

*Department of Chemistry, The City College of the City University of New York, Convent Avenue @ 138th Street, New York, NY 10031, U.S.A.


The first successful reductions of the aromatic rings of phthalides, with the preservation of the lactone rings, are reported. The reduction/alkylation of some substituted 4-methoxyphthalides gave lactonic enol ethers, which were converted into conjugated homocyclic dienes and further into cyclohexenones. These enones were easily converted into bicyclo[3.2.1]octanes by the Bu3SnH/AIBN free radical cyclization reaction.