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Paper | Special issue | Vol 61, No. 1, 2003, pp.113-123
Published online, 13th May, 2003
DOI: 10.3987/COM-03-S3
Synthesis and Bridgehead Reactions of 9-Substituted 5,6,7,8,9,10-Hexahydro-5,9-Methanopyrimido[4,5-b]azocin-4(3H)-ones

Edward C. Taylor* and Beena Bhatia

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, U.S.A.


The condensation of a variety of 6-amino-4(3H)-pyrimidinones with 2-cyclohexen-1-one in water, and replacement of the bridgehead 9-hydroxy group in the resulting Michael/cyclization adducts with carbon nucleophiles, are described. These reactions have been exploited for the preparation of a novel bridged tricyclic analog of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF).